7# ,]*+!;((((((X((())()>)>z)x(*0 *P***(**h***.******Experiment II Determination of the Elemental Molar Masses of Chlorine and Bromine PRE-LAB ASSIGNMENT Reading: Before coming to your discussion section, read the following: 1. Sections 2.1 through 2.3, and 3.4 in Olmstead and Williams. 2. The remainder of this experiment in this manual. Pre-lab assignment to hand in: Provide your instructor with written responses to the following questions at the beginning of your discussion period: 1. Why dont we use pure CH3Cl in these experiments? 2. What is the gas chromatograph used for in this experiment? 3. What fragment of BF3 could be responsible for the mass 30 peak in Figure 2? 4. The data analysis for this experiment would be much more difficult if we used Cl2 as the sample instead of CH3Cl. Why? INTRODUCTION The purpose of this lab is to help you discover what is meant by elemental molar mass. Many elements have more than one stable isotope. As a result, individual atoms of the same element can have different masses. In the laboratory we are almost always working with large numbers of atoms (moles). We are, therefore, interested in the average mass of a mixture of stable isotopes of the element, rather than the individual isotope masses. In this lab you will use a mass spectrometer to measure the masses and abundances of the isotopes of Cl (35Cl and 37Cl) and Br (79Br and 81Br). From the mass and abundance data you will be able to calculate the elemental molar mass of Cl and Br and compare your answer to the published result. This experiment is a "discovery"-type experiment. The procedure will be carefully described, but the analysis of the data is left purposely vague. You will work in small groups to decide how best to work up the data. In the process you will have the chance to discover some principles, to use what you have learned in lecture, and to practice thinking about manipulative details and theory at the same time. What is a mass spectrometer? A mass spectrometer is an instrument that accurately measures the masses and relative abundances of atoms, molecules, or pieces of molecules (fragments). Figure 1 is a diagram of our instrument. A mass spectrometer consists of three general parts: the ion source, the mass separator, and the ion detector. In our instrument a sample is introduced into the ion source as a gas. An electron beam fragments the gas molecules into positively charged ions. The positive ions are accelerated away from the positively charged accelerator plate, through a set of charged focusing lenses and into the mass separator. A mass separator consists of a magnetic field that deflects ions toward or away from the detector. A schematic of a simple mass separator is shown in Figure 2-24 of your text. Figure 1 shows a slightly more complicated mass separator used in our instrument at Colby. {In our instrument, the magnet is actually a set of four electromagnets called a quadrupole. The quadrupole magnet oscillates very quickly causing the positively charged fragments to travel in an oscillating path. Only fragments with the correct mass can travel the entire length of the quadrupole magnet without hitting the walls of the instrument.} Ion fragments that pass through the mass separator hit a detector where a small current is produced and recorded by a computer. By changing the magnet field strength of the mass separator fragments of different masses can be detected. Analysis of mass spectral data is often used to determine the structure of unknown compounds.  Figure 2 shows the mass spectrum of the gas boron trifluoride, BF3. The spectrum is a plot of fragment abundance as a function of mass number. Each vertical bar corresponds to a fragment ion, the position denotes its mass and the height is proportional to the abundance of the ion. Because boron has two stable isotopes, 10B and 11B, the BF3+ fragment produces peaks at 67 and 68 mass number (fluorine has only one stable isotope with a mass of 19). Similarly the BF2+ fragment produces two peaks with similar relative abundances at 48 and 49 mass number. The difference between the two sets of peaks is the loss of a single fluorine. Notice a fragment peak at 19 mass number due to a F+ fragment. Using the mass spectral data, the elemental abundances of 10B to 11B can also be calculated. Example for 10B. Fragment Mass number Relative Abundance 10BF2+ 48 2692 11BF2+ 49 10000 ````````````````````````````````````````` total BF2+ 48 + 49 2692 + 10000 The fluorine has only one stable isotope so it plays no role in the calculations. The elemental abundance of 10B is determined from the relative abundance of 10BF2+ divided by the total fragment abundance. Abundance 10B % = F(rel.ab. 10BF2+,total frag. ab.) x 100 = F(2692,(2692 + 10000)) x 100 = 21.21% If the abundances and masses of the two boron isotopes are known, the elemental molar mass for the element can be calculated as a weighted average.  Outline of this experiment. You will work in pairs to determine the elemental molar mass for chlorine and bromine. The samples you will be using are the gasses chloromethane, CH3Cl, and bromomethane, CH3Br. Because the gases are very reactive in the pure form and difficult to handle, we have purchased the gases dissolved in tert-butyl methyl ether. A small amount of the gas-ether solution will be provided in a small vial. The ether rapidly evaporates in the vial so you will really have a sample of CH3Br or CH3Cl gas mixed with gaseous ether. The first step in the analysis will be to separate the CH3Br or CH3Cl from the ether. The second step of the experiment will be to take the mass spectrum of the pure CH3Br or CH3Cl sample. The separation of the gas mixtures will be performed using a gas chromatograph (GC). A GC separates gas mixtures based on boiling point. High boiling compounds take longer to pass through the GC than low boiling compounds. In our experiment, CH3Cl or CH3Br leave the GC first. The separated gases from the GC are then automatically introduced into the mass spectrometer (MS) for analysis. The combination of a gas chromatograph and a mass spectrometer is referred to as a GC-MS. Using the mass spectral data for CH3Br and CH3Cl you and your partner will calculate the elemental molar mass for chlorine and bromine. You will then compare your results with the reported result on the front cover of your textbook. PROCEDURE 1. Work alone or in pairs. 2. Sign up for a GC-MS time slot on the black board at the front of the laboratory. 3. You will be analyzing two samples, a CH3Br and ether gas mixture and a CH3Cl and ether gas mixture. The samples will be contained in labeled, 40-mL sampling vials. Check with the lab instructor to make sure the GC-MS is ready for a new sample. Click with the LEFT mouse button on the Acquisition window. Pull down the ACQUIRE DATA menu and select ACQUIRE DATA. Enter a file name for your sample and hit return. The GC-MS is now ready to run your sample. Select a sample and insert the needle of a 10-ml syringe through the septa on the top of the sample vial. Gently pull the plunger of the syringe upward to draw 5-10 ml of the GAS MIXTURE into the syringe. 4. Remove the syringe needle from the sample vial and GENTLY push the syringe needle into the injection port of the GC. Push the START button on the front of the GC to start the analysis.  5. The instrument is fully automated, so stand back and watch the system acquire your data. The computer system next to the GC-MS will display a plot showing total ion counts (TIC) as a function of time similar to plot shown in Figure 3. The TIC is the sum of all fragments abundances at a given time. Different compounds come off the GC at different times and therefore produce different peaks. The samples we are interested in (CH3Cl or CH3Br) boil at very low temperatures and therefore come off the GC very quickly. The ether will come off the GC second. After the GC run is complete the TIC plot will disappear. Click on the DATA ANALYSIS window to look at your data. Load your data by pulling down the FILE menu and selecting LOAD. Select your data file. Your data (TIC plot) will appear on the screen. Double click the RIGHT mouse button on a peak to display the mass spectrum of the compound that produced the peak. Print the TIC plot and the mass spectrum of CH3Cl or CH3Br by pulling down the FILE menu with the LEFT mouse button and selecting PRINT. You can ask the computer program to tabulate the mass number and relative abundance for the selected mass spectrum by pulling down the SPECTRUM menu and selecting TABULATE. Print the tabulated mass spectral data for CH3Cl or CH3Br by selecting PRINT. 6. A mass spectrum of a compound provides a chemical "fingerprint" since the fragmentation pattern for each compound is unique. Our GC-MS software has a library of mass spectra ("fingerprints") for 70,000 compounds. Double click the RIGHT mouse button on the mass spectra of your sample to perform a library search of your sample against the 70,000 known compounds. The search should produce methane, -bromo or methane, -chloro as a result. While we know the identity of the compounds used in this lab, you can imagine how helpful this search capability might be to an analytical lab doing drug testing, for example. 7. Repeat steps 3-6 with the other sample. DATA ANALYSIS 1. Working with your partner, use the mass spectral data for CH3Cl and CH3Br to calculate the elemental molar mass for chlorine and bromine. 2. Compare your results with the reported results on the front cover of your textbook. 3. Calculate the percent error in your results. 4. Speculate on the sources of the error in your experiment. 5. Turn in a sheet of paper with the results of your calculations before you leave the laboratory. If you have difficulty with the calculations feel free to consult with your lab instructor often, but don't be frustrated if your instructor doesn't answer all of your questions or asks a question in return. You will have a better sense of accomplishment if you work out the details on your own. You will hopefully gain a better grasp of the theory of this experiment if you try many ideas, some of which might be wrong. LABORATORY NOTEBOOK Keep track of all measurements in your lab notebook. Record all observations and tape copies of ALL DATA in your lab notebook. Both members of the group should keep track of the various calculations that you tried, in their notebooks. Do all of your calculations in your lab notebooks. REPORT 1. Turn in an exact photocopy of your laboratory notebook (this lab only). 2. Clearly circle your result for the elemental molar mass for chlorine and bromine. 3. Give the name of your lab partner. Appendix: Structures of the compounds used in this laboratory.  CH 141 Lab: Expt. II -- -- CH 141 Lab: Expt. 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Round rect 1 w 0 G 0 g 0 0 0 0 cmyk 0 0 0 1 CMYK 129 138 m 460 138 L 468.883 137.996 476 145.113 476 154 c 476 203 L 476 211.883 468.883 219 460 219 c 129 219 L 120.113 219 112.996 211.883 112.996 203 c 113 154 L 112.996 145.113 120.113 137.996 128.996 137.996 c gsave f grestore s % Round rect 1 w 0 G 0.5 g 0 0 0 1 cmyk 0 0 0 1 CMYK 197 145 m 413 145 L 414.109 144.996 415 145.887 415 147 c 415 151 L 415 152.109 414.109 153 413 153 c 197 153 L 195.887 153 194.996 152.109 194.996 151 c 195 147 L 194.996 145.887 195.887 144.996 197 144.996 c gsave f grestore s % Round rect 1 w 0 G 0.5 g 0 0 0 1 cmyk 0 0 0 1 CMYK 196 203.5 m 412 203.5 L 413.109 203.496 414 204.387 414 205.5 c 414 209.5 L 414 210.609 413.109 211.5 412 211.5 c 196 211.5 L 194.887 211.5 193.996 210.609 193.996 209.5 c 194 205.5 L 193.996 204.387 194.887 203.496 196 203.496 c gsave f grestore s % Round rect 1 w 0 G 0.5 g 0 0 0 0 cmyk 0 0 0 1 CMYK 78 176 m 122 176 L 123.109 175.996 124 176.887 124 178 c 124 182 L 124 183.109 123.109 184 122 184 c 78 184 L 76.887 184 75.996 183.109 75.996 182 c 76 178 L 75.996 176.887 76.887 175.996 77.996 175.996 c gsave f grestore s % Oval 1 w 0 G 0 g 0 0 0 1 cmyk 0 0 0 1 CMYK 79.5 175.996 m 81.441 175.996 83 177.996 83 180.5 c 83 183 81.441 185 79.5 185 c 77.555 185 75.996 183 75.996 180.5 c 75.996 177.996 77.555 175.996 79.496 175.996 c gsave F grestore S % Oval 1 w 0 g 0 0 0 1 cmyk 0 0 0 1 CMYK 135 158.996 m 139.996 158.996 144 169.668 144 183 c 144 196.328 139.996 207 135 207 c 130 207 125.996 196.328 125.996 183 c 125.996 169.668 130 158.996 134.996 158.996 c F % Oval 1 w 0 G 0 g 0 0 0 0 cmyk 0 0 0 1 CMYK 130 153.996 m 134.996 153.996 139 164.668 139 178 c 139 191.328 134.996 202 130 202 c 125 202 120.996 191.328 120.996 178 c 120.996 164.668 125 153.996 129.996 153.996 c gsave F grestore S % Oval 1 w 0 g 0 0 0 1 cmyk 0 0 0 1 CMYK 444 159.496 m 451.773 159.496 458 170.168 458 183.5 c 458 196.828 451.773 207.5 444 207.5 c 436.223 207.5 429.996 196.828 429.996 183.5 c 429.996 170.168 436.223 159.496 443.996 159.496 c F % Oval 1 w 0 G 0.875 g 0 0 0 1 cmyk 0 0 0 1 CMYK 439 154.496 m 446.773 154.496 453 165.168 453 178.5 c 453 191.828 446.773 202.5 439 202.5 c 431.223 202.5 424.996 191.828 424.996 178.5 c 424.996 165.168 431.223 154.496 438.996 154.496 c gsave F grestore S % Bezier 1 w 0 G 0 0 0 0 cmyk 0 0 0 1 CMYK 189.988 177.5 m 190.977 177.5 207.664 140 225.34 177.5 c 243.008 215 263.625 178.344 261.66 178.344 c 259.695 178.344 276.391 143.402 296.023 177.5 c 315.66 211.582 331.363 177.5 331.363 177.5 c 331.363 177.5 347.074 145.102 366.707 177.5 c 386.344 209.883 401.07 178.344 402.047 177.5 c 403.031 176.645 415.793 144.258 437.391 176.645 c S % Line 0 G 3 w 0 0 0 1 CMYK 134 208 m 134 233 L S gsave newpath 123 232 m 144 232 L 144 262 L 123 262 L closepath eoclip [1 0 0 1 123 232 ] concat fnt__2 [28 0 0 28 0 0] makefont setfont 0 0 0 1 setcmykcolor 4 (+) {show} 23 0 tx grestore % Arrow % Polygon 1 w 0 G 0 g 0 0 0 0 cmyk 0 0 0 1 CMYK 154.938 125.418 m 153.023 128.926 L 161 131 L 154.938 125.418 L gsave f grestore s % Line 0 G 1 w 0 0 0 1 CMYK 153.98 127.172 m 139 119 L S % Arrow % Polygon 1 w 0 G 0 g 0 0 0 0 cmyk 0 0 0 1 CMYK 116.68 157.703 m 114.344 160.945 L 122 164 L 116.68 157.703 L gsave f grestore s % Line 0 G 1 w 0 0 0 1 CMYK 115.512 159.324 m 79 133 L S % Arrow % Polygon 1 w 0 G 0 g 0 0 0 0 cmyk 0 0 0 1 CMYK 428.641 216.262 m 432.211 218.043 L 434 210 L 428.641 216.262 L gsave f grestore s % Line 0 G 1 w 0 0 0 1 CMYK 430.426 217.152 m 406 266 L S % Arrow % Polygon 1 w 0 G 0 g 0 0 0 0 cmyk 0 0 0 1 CMYK 66.078 177.855 m 65.93 185.848 L 74 182 L 66.078 177.855 L gsave f grestore s % Line 0 G 1 w 0 0 0 1 CMYK 66.004 181.852 m 21 181 L S gsave newpath 269 115 m 393 115 L 393 133 L 269 133 L closepath eoclip [1 0 0 1 269 115 ] concat fnt__1 [14 0 0 14 0 0] makefont setfont 0 0 0 1 setcmykcolor 112.434 106.223 99.223 92.223 86.012 73.57 70.07 63.859 59.973 52.973 45.973 38.973 34.316 27.316 21.105 14.105 4 (Quadrupole Magnet) {show} 14 0 tx grestore gsave newpath 13 192 m 98 192 L 98 226 L 13 226 L closepath eoclip [1 0 0 1 13 192 ] concat fnt__1 [14 0 0 14 0 0] makefont setfont 0 0 0 1 setcmykcolor 62.684 58.797 51.797 40.91 34.699 29.258 25.758 20.316 14.105 4 (Gas sample) {show} 14 0 tx 24.984 18.773 14.887 7.887 4 (inlet) {show} 30 0 tx grestore gsave newpath 11 111 m 99 111 L 99 147 L 11 147 L closepath eoclip [1 0 0 1 11 111 ] concat fnt__1 [14 0 0 14 0 0] makefont setfont 0 0 0 1 setcmykcolor 68.477 61.477 57.59 53.703 47.492 42.836 36.625 32.738 26.527 20.316 14.105 4 (Accelerating) {show} 14 0 tx 24.984 21.098 14.887 11 4 (plate) {show} 30 0 tx grestore gsave newpath 96 87 m 162 87 L 162 121 L 96 121 L closepath eoclip [1 0 0 1 96 87 ] concat fnt__1 [14 0 0 14 0 0] makefont setfont 0 0 0 1 setcmykcolor 44.402 37.402 32.746 28.859 22.648 16.438 12.551 4 (Electron) {show} 14 0 tx 25.758 19.547 13.336 4 (Beam) {show} 30 0 tx grestore % Arrow % Polygon 1 w 0 G 0 g 0 0 0 0 cmyk 0 0 0 1 CMYK 286.258 183.344 m 290.148 184.242 L 290 176 L 286.258 183.344 L gsave f grestore s % Line 0 G 1 w 0 0 0 1 CMYK 288.203 183.793 m 269 267 L S gsave newpath 233 267 m 337 267 L 337 303 L 233 303 L closepath eoclip [1 0 0 1 233 267 ] concat fnt__1 [14 0 0 14 0 0] makefont setfont 0 0 0 1 setcmykcolor 47.145 40.145 36.645 25.758 19.547 13.336 4 (Beam of) {show} 14 0 tx 69.699 62.699 55.699 51.812 48.312 42.102 35.102 31.215 27.328 23.441 18 11 4 (positive ions) {show} 30 0 tx grestore gsave newpath 16.5 313.5 m 492.5 313.5 L 492.5 347.5 L 16.5 347.5 L closepath eoclip [1 0 0 1 16.5 313.5 ] concat fnt__2 [14 0 0 14 0 0] makefont setfont 0 0 0 1 setcmykcolor 54.141 47.141 43.641 37.43 31.219 23.438 16.438 12.551 4 (Figure 1.) {show} 14 0 tx fnt__1 [14 0 0 14 0 0] makefont setfont 440.035 433.035 426.035 422.535 415.535 408.535 405.035 398.035 391.824 386.383 379.383 375.883 371.227 365.016 358.805 351.805 347.918 341.707 334.707 328.496 324.996 319.555 314.113 307.902 297.016 293.516 287.305 283.418 276.418 269.418 262.418 257.762 250.762 244.551 237.551 230.551 227.051 220.84 217.34 212.684 205.684 202.184 195.184 188.184 184.297 180.41 174.199 170.312 163.312 157.102 151.66 145.449 140.793 133.793 127.582 122.926 119.426 113.215 109.328 105.441 99.23 88.344 82.133 75.133 68.922 61.141 57.641 ( Schematic representation of a quadrupole mass analyzer used on our) {show} 14 0 tx 231.715 227.059 220.848 216.961 210.75 199.863 192.863 188.207 184.32 178.109 171.898 164.898 159.457 155.957 150.516 145.074 138.863 127.977 124.477 117.477 110.477 103.477 96.477 92.977 85.977 81.32 75.109 68.109 61.898 55.688 47.906 44.406 40.52 34.309 30.422 20.316 14.105 4 (Hewlet Packard 5970 mass spectrometer.) {show} 30 0 tx grestore % Round rect 1 w 0 G 0 g 0 0 0 1 cmyk 0 0 0 1 CMYK 188 146 m 190 146 L 190.555 145.996 191 146.441 191 147 c 191 173 L 191 173.555 190.555 174 190 174 c 188 174 L 187.441 174 186.996 173.555 186.996 173 c 187 147 L 186.996 146.441 187.441 145.996 188 145.996 c gsave f grestore s % Round rect 1 w 0 G 0 g 0 0 0 1 cmyk 0 0 0 1 CMYK 187 185.5 m 189 185.5 L 189.555 185.496 190 185.941 190 186.5 c 190 212.5 L 190 213.055 189.555 213.5 189 213.5 c 187 213.5 L 186.441 213.5 185.996 213.055 185.996 212.5 c 186 186.5 L 185.996 185.941 186.441 185.496 187 185.496 c gsave f grestore s % Group % Oval 1 w 0 G 0 g 0 0 0 0 cmyk 0 0 0 1 CMYK 169.5 134.246 m 173.246 134.246 176.25 135.805 176.25 137.75 c 176.25 139.691 173.246 141.25 169.5 141.25 c 165.75 141.25 162.746 139.691 162.746 137.75 c 162.746 135.805 165.75 134.246 169.496 134.246 c gsave F grestore S % Rect 1 w 0 G 0.25 g 0 0 0 0 cmyk 0 0 0 1 CMYK 163 115 m 176 115 L 176 138 L 163 138 L 163 115 L gsave f grestore s % Oval 1 w 0 G 0.25 g 0 0 0 0 cmyk 0 0 0 1 CMYK 169.5 111.246 m 172.969 111.246 175.75 112.582 175.75 114.25 c 175.75 115.914 172.969 117.25 169.5 117.25 c 166.027 117.25 163.246 115.914 163.246 114.25 c 163.246 112.582 166.027 111.246 169.496 111.246 c gsave F grestore S % Oval 1 w 0.281 G 0.25 g 0 0 0 0 cmyk 0 0 0 0 CMYK 169.5 134.496 m 172.691 134.496 175.25 135.832 175.25 137.5 c 175.25 139.164 172.691 140.5 169.5 140.5 c 166.305 140.5 163.746 139.164 163.746 137.5 c 163.746 135.832 166.305 134.496 169.496 134.496 c gsave F grestore S % Line 0 G 1 w 0 0 0 1 CMYK 165.5 143.5 m 160.5 187.5 L [1 2 ] 0 d S 0 J [] 0 d % Line 0 G 1 w 0 0 0 1 CMYK 168.75 142.75 m 171.25 203.5 L [1 2 ] 0 d S 0 J [] 0 d % Line 0 G 1 w 0 0 0 1 CMYK 173.25 142.75 m 175.5 179.75 L [1 2 ] 0 d S 0 J [] 0 d % Line 0 G 1 w 0 0 0 1 CMYK 166.75 142 m 164.25 205.75 L [1 2 ] 0 d S 0 J [] 0 d % Line 0 G 1 w 0 0 0 1 CMYK 162.75 142.5 m 152.5 203.25 L [1 2 ] 0 d S 0 J [] 0 d % Line 0 G 1 w 0 0 0 1 CMYK 170.75 143 m 176 212.5 L [1 2 ] 0 d S 0 J [] 0 d % Line 0 G 1 w 0 0 0 1 CMYK 174.75 144.5 m 178.75 191.25 L [1 2 ] 0 d S 0 J [] 0 d % Oval 2 w 0 G 0 g 0 0 0 0 cmyk 0 0 0 1 CMYK 131 173.996 m 133.219 173.996 135 177.109 135 181 c 135 184.887 133.219 188 131 188 c 128.777 188 126.996 184.887 126.996 181 c 126.996 177.109 128.777 173.996 130.996 173.996 c gsave F grestore S % Line 0.25 G 5 w 0 0 0 1 CMYK 133 181 m 187 181 L S gsave newpath 163 266 m 229 266 L 229 300 L 163 300 L closepath eoclip [1 0 0 1 163 266 ] concat fnt__1 [14 0 0 14 0 0] makefont setfont 0 0 0 1 setcmykcolor 48.32 41.32 37.434 31.992 24.992 18.781 11.781 4 (Focusing) {show} 14 0 tx 48.293 44.406 37.406 31.195 20.309 14.098 10.211 4 (elements) {show} 30 0 tx grestore % Arrow % Polygon 1 w 0 G 0 g 0 0 0 0 cmyk 0 0 0 1 CMYK 182.168 221.742 m 186.145 222.164 L 185 214 L 182.168 221.742 L gsave f grestore s % Line 0 G 1 w 0 0 0 1 CMYK 184.156 221.953 m 180 261 L S % Oval 1 w 0 G 0 0 0 0 cmyk 0 0 0 1 CMYK 133.5 234.996 m 140.441 234.996 146 240.555 146 247.5 c 146 254.441 140.441 260 133.5 260 c 126.555 260 120.996 254.441 120.996 247.5 c 120.996 240.555 126.555 234.996 133.496 234.996 c S % Rect 1 w 0 G 0 g 0 0 0 0 cmyk 0 0 0 1 CMYK 488.668 140 m 535.668 140 L 535.668 212 L 488.668 212 L 488.668 140 L gsave f grestore s gsave newpath 501.996 123.332 m 519.996 123.332 L 519.996 206.664 L 501.996 206.664 L closepath eoclip [0 -1.004 1 0 501.996 206.664 ] concat fnt__1 [14 0 0 14 0 0] makefont setfont 0 0 0 1 setcmykcolor 55.32 49.109 45.223 38.223 31.223 20.336 13.336 4 (Computer) {show} 14 0 tx grestore % Line 0 G 3 w 0 0 0 1 CMYK 458.664 180 m 488 180 L S %%Trailer end NN e e   e,Times .+ ,  Helvetica) ) "1T8"Q"Q"Q"Q"Q"Q"Q"Q"Q"Q"yQ"sQ"nQ"hQ"bQ"]Q"WQ"QQ"LQ"FQ"@Q";Q"5Q"/Q"*Q"$Q"Q"Q"Q" Q"Q"Q"Q"Q"Q"Q"Q"Q"Q"Q"Q"Q"Q"Q"Q"Q"Q"Q"Q"Q"Q"T"_"k"v""""""""""""" ""!","8"C"N"Z"e"q"|""""""""""N"N"yN"]N"@N"$N"N"N"N"N"N"T""""8"q"" TT T"Y""""""" """"""" "" "+"H"M"S"Y"^"ddM jj""""" (E0(01000(~02000(a03000(E04000((05000( 06000(07000(08000(09000()10000(Q0)510)920)930)940)950)860)9709 ((Relative Abundance  ess^'  `? ?p 0 p0'  `? @!!!? ( Mass Number A%KPA FKH (410 + BF+2(4?+qVX_`V^[X_`V^pVX_`V^[X_`V^"Y[qpysypsppysyps"vqp"qp"qp"(Figure 2)2. Mass Spectrum of BF +3 (3. Prominent peaks are labeled with the appropriate(positively charged fragments.AAH (1)1 +BF+2(+qp"qp"Ai]AdXzH (uZ10 + B(up+AUtAPoH (a11 + B(a+AaA\{H+>F(i+A7]A2XH (F11 + BF+3(F+Ab{A]vH (qx10 + BF+3(q+'%!PS-Adobe-2.0 EPSF-1.2 %%Creator: DeltaGraph Professional 3.0 %%Title: (BF3 Mass Spec Figure:Chart View) %%Creation Date: (8/24/94) (10:39 PM) %%BoundingBox: 23 203 612 585 %%DocumentProcSets: DeltaGraph 3.0 %%DocumentSuppliedProcSets: DeltaGraph 3.0 %%DocumentProcessColors: Cyan Magenta Yellow Black %%DocumentFonts: Times-Roman %%+Helvetica %%+Times-Bold %%EndComments %%BeginProcSet: DeltaGraphPro /DeltaGraphPro 200 dict def DeltaGraphPro begin /currentpacking where{pop true setpacking}if /Version 3.0 def /Revision 13 def /PSL2 /languagelevel where{pop languagelevel}{1}ifelse 2 ge def /bdef{bind def}bind def /ldef{load def}bdef /xdef{exch def}bdef /SYM -987654321.1 def /setcmykcolor where dup not{/setcmykcolor{1 sub 4 1 roll 3 {3 index add neg dup 0 lt{pop 0}if 3 1 roll}repeat setrgbcolor pop}def}if{pop}if /colorimage where dup not{/colorimage{}def}if{pop}if /FillGray 0 def /FillCyan 0 def /FillMagenta 0 def /FillYellow 0 def /FillBlack 1 def /FillMac 8 string def /UseMacFill false def /StrokeGray 0 def /StrokeCyan 1 def /StrokeMagenta 1 def /StrokeYellow 1 def /StrokeBlack 1 def /StrokeMac 8 string def /UseMacStroke false def /savestate{FillGray FillCyan FillMagenta FillYellow FillBlack FillMac UseMacFill StrokeGray StrokeCyan StrokeMagenta StrokeYellow StrokeBlack StrokeMac UseMacStroke}bdef /restorestate{/UseMacStroke xdef /StrokeMac xdef /StrokeBlack xdef /StrokeYellow xdef /StrokeMagenta xdef /StrokeCyan xdef /StrokeGray xdef /UseMacFill xdef /FillMac xdef /FillBlack xdef /FillYellow xdef /FillMagenta xdef /FillCyan xdef /FillGray xdef}bdef /cmyk{/FillBlack xdef /FillYellow xdef/FillMagenta xdef/FillCyan xdef}bdef /CMYK{/StrokeBlack xdef /StrokeYellow xdef/StrokeMagenta xdef/StrokeCyan xdef}bdef /apat 8 string def/mat matrix def 1 0 mat defaultmatrix dtransform exch atan/patang xdef /sscrn{currentscreen/proc xdef/ang xdef/freq xdef}bdef /rscrn{freq ang/proc load setscreen}bdef /macpat{apat copy pop 9.375 patang {1 add 4 mul cvi apat exch get exch 1 add 4 mul cvi 7 sub bitshift 1 and}setscreen setgray}bdef /d/setdash ldef /g{false/UseMacFill xdef/FillGray xdef}bdef /mg{true/UseMacFill xdef FillMac copy pop/FillGray xdef}bdef /G{false/UseMacStroke xdef/StrokeGray xdef}bdef /MG{true/UseMacStroke xdef StrokeMac copy pop/StrokeGray xdef}bdef /_i currentflat def /i{dup 0 eq{pop _i}if setflat}bdef /j/setlinejoin ldef /J/setlinecap ldef /M/setmiterlimit ldef /w/setlinewidth ldef /_R{.25 sub round .25 add}bdef /_r{transform _R exch _R exch itransform}bdef /m{_r moveto}bdef /L{_r lineto}bdef /c{_r curveto}bdef /_gf{1.0 FillGray sub mul}bdef /_gs{1.0 StrokeGray sub mul}bdef /sf{UseMacFill{FillCyan FillMagenta FillYellow FillBlack setcmykcolor sscrn FillGray FillMac macpat}{FillGray setgray FillCyan _gf FillMagenta _gf FillYellow _gf FillBlack _gf setcmykcolor}ifelse}bdef /ss{UseMacStroke{StrokeCyan StrokeMagenta StrokeYellow StrokeBlack setcmykcolor sscrn StrokeGray StrokeMac macpat}{StrokeGray setgray StrokeCyan _gs StrokeMagenta _gs StrokeYellow _gs StrokeBlack _gs setcmykcolor}ifelse}bdef /F{sf eofill UseMacFill{rscrn}if}bdef /f{closepath F}bdef /S{ss stroke UseMacStroke{rscrn}if}bdef /s{closepath S}bdef /B{gsave F grestore S}bdef /b{closepath B}bdef /N/newpath ldef /n/N ldef /sh{currentpoint 3 -1 roll show 3 -1 roll add moveto}bdef /NewCodes 256 array def /NUL/SOH/STX/ETX/EOT/ENQ/ACK/BEL/BS/HT/LF/VT/FF/CR/SO/SI /DLE/DC1/DC2/DC3/DC4/NAK/SYN/ETB/CAN/EM/SUB/ESC/FS/GS/RS/US NewCodes 0 32 getinterval astore pop NewCodes 32/Times-Roman findfont/Encoding get 32 96 getinterval putinterval NewCodes dup 39/quotesingle put 96/grave put /Adieresis/Aring/Ccedilla/Eacute/Ntilde/Odieresis/Udieresis/aacute /agrave/acircumflex/adieresis/atilde/aring/ccedilla/eacute/egrave /ecircumflex/edieresis/iacute/igrave/icircumflex/idieresis/ntilde/oacute /ograve/ocircumflex/odieresis/otilde/uacute/ugrave/ucircumflex/udieresis /dagger/degree/cent/sterling/section/bullet/paragraph/germandbls /registered/copyright/trademark/acute/dieresis/notequal/AE/Oslash /infinity/plusminus/lessequal/greaterequal/yen/mu/partialdiff/summation /product/pi/integral/ordfeminine/ordmasculine/Omega/ae/oslash /questiondown/exclamdown/logicalnot/radical/florin/approxequal/Delta/guillemotleft /guillemotright/ellipsis/blank/Agrave/Atilde/Otilde/OE/oe /endash/emdash/quotedblleft/quotedblright/quoteleft/quoteright/divide/lozenge /ydieresis/Ydieresis/fraction/currency/guilsinglleft/guilsinglright/fi/fl /daggerdbl/periodcentered/quotesinglbase/quotedblbase/perthousand/Acircumflex /Ecircumflex/Aacute /Edieresis/Egrave/Iacute/Icircumflex/Idieresis/Igrave/Oacute/Ocircumflex /apple/Ograve/Uacute/Ucircumflex/Ugrave/dotlessi/circumflex/tilde /macron/breve/dotaccent/ring/cedilla/hungarumlaut/ogonek/caron NewCodes 128 128 getinterval astore pop /oshow{/str2 xdef .1 w 0 1 str2 length 1 sub{str2 exch 1 getinterval false charpath currentpoint stroke m}for}bdef /ktx{newpath /$1 xdef /$2 xdef /$3 xdef /$4 xdef $3 $2 moveto $4 show $1 0 gt{$1 2 div w 0 $1 rmoveto $3 $2 $1 add lineto stroke}if}bdef /tx{newpath /$1 xdef /$2 xdef /$3 xdef /$4 xdef dup /$5 xdef 0 1 $4 length 1 sub{$4 exch 1 getinterval exch $2 moveto $3}for $1 0 gt{$1 2 div w 0 $1 rmoveto $5 $2 $1 add lineto stroke}if}bdef /stx{newpath /$1 xdef /$2 xdef /$3 xdef /$4 xdef dup /$5 xdef 0 1 $4 length 1 sub{$4 exch 1 getinterval exch dup SYM eq{pop exch $2 moveto currentfont SymbolFont setfont exch $3 setfont}{$2 moveto $3}ifelse}for}bdef /showsym{moveto gsave /ch xdef currentpoint initmatrix translate 0 0 moveto currentfont /FontName get /Courier eq ch exch charpath flattenpath pathbbox /ury xdef /urx xdef /lly xdef /llx xdef urx llx sub -2 div llx sub ury lly sub -2 div lly sub grestore rmoveto ch show}def /ps2mac{1 -1 scale neg 0 exch translate}bdef /mac2ps{0 exch translate 1 -1 scale}bdef /xpat{gsave setcmykcolor eofill grestore gsave FillCyan FillMagenta FillYellow FillBlack setcmykcolor eoclip /thepat xdef /right xdef/bottom xdef/left xdef/top xdef /sizev xdef /sizeh xdef /shrink exch 72 div def /howmanywide left right sub abs cvi sizeh idiv 1 add shrink mul 1 add cvi def /howmanydown bottom top sub abs cvi sizev idiv 1 add shrink mul 1 add cvi def left top translate sizeh shrink div sizev shrink div scale howmanydown{gsave howmanywide{sizeh sizev true [sizeh 0 0 sizev 0 0]{thepat}imagemask 1 0 translate}repeat grestore 0 1 translate}repeat grestore}bdef /drawrect{/$r xdef /$b xdef /$l xdef /$t xdef $l $t m $r $t L $r $b L $l $b L closepath}bdef /drawdiamond{/$r xdef /$b xdef /$l xdef /$t xdef $l $r add 2 div $t m $l $t $b add 2 div L $l $r add 2 div $b L $r $t $b add 2 div L closepath}bdef /ellipse{newpath/savematrix matrix currentmatrix def translate scale 0 0 1 5 -2 roll arc savematrix setmatrix}bdef /drawcircle{/$r xdef /$b xdef /$l xdef /$t xdef 0 360 $r $l sub 2 div $t $b sub 2 div $r $l add 2 div $b $t add 2 div ellipse}bdef /dofill{gsave 1 setlinewidth eoclip /$drawit xdef /$steps xdef /$cv xdef /$ch xdef /$r xdef /$b xdef /$l xdef /$t xdef /$tstep $t $cv sub $steps div def /$bstep $b $cv sub $steps div def /$lstep $l $ch sub $steps div def /$rstep $r $ch sub $steps div def dup /$black xdef exch sub $steps div /$blackStep xdef dup /$yellow xdef exch sub $steps div /$yellowStep xdef dup /$magenta xdef exch sub $steps div /$magentaStep xdef dup /$cyan xdef exch sub $steps div /$cyanStep xdef newpath 0 1 $steps{pop $cyan $magenta $yellow $black setcmykcolor $t $l $b $r $drawit eofill /$t $t $tstep sub def /$l $l $lstep sub def /$b $b $bstep sub def /$r $r $rstep sub def /$cyan $cyan $cyanStep sub def /$magenta $magenta $magentaStep sub def /$yellow $yellow $yellowStep sub def /$black $black $blackStep sub def}for grestore}bdef /dolfill{gsave 1 setlinewidth eoclip 1 sub /$steps xdef /$r xdef /$b xdef /$l xdef /$t xdef /$type xdef 1 eq /$isdouble xdef dup /$black xdef exch sub $steps div /$blackStep xdef dup /$yellow xdef exch sub $steps div /$yellowStep xdef dup /$magenta xdef exch sub $steps div /$magentaStep xdef dup /$cyan xdef exch sub $steps div /$cyanStep xdef $type 1 eq{/$fromx $l def /$fromy $t def /$tox $r def /$toy $t def /$stepx 0 def /$stepy $t $b sub $steps div $isdouble{2 div}if def $stepx abs $stepy abs gt{$stepx}{$stepy}ifelse abs setlinewidth}if $type 2 eq{/$fromx $l def /$fromy $t def /$tox $l def /$toy $b def /$stepx $r $l sub $steps div $isdouble{2 div}if def /$stepy 0 def $stepx abs $stepy abs gt{$stepx}{$stepy}ifelse abs setlinewidth}if $type 3 eq{/$fromx $l $r $l sub 2 div sub def /$fromy $t $b add 2 div def /$tox $r $l add 2 div def /$toy $t $t $b sub 2 div add def /$stepx $r $l sub $steps div $isdouble{2 div}if def /$stepy $t $b sub $steps div $isdouble{2 div}if def $stepx abs $stepy abs gt{$stepx}{$stepy}ifelse abs 2 mul setlinewidth}if $type 4 eq{/$fromx $r $r $l sub 2 div add def /$fromy $t $b add 2 div def /$tox $r $l add 2 div def /$toy $t $t $b sub 2 div add def /$stepx $r $l sub $steps div neg $isdouble{2 div}if def /$stepy $t $b sub $steps div $isdouble{2 div}if def $stepx abs $stepy abs gt{$stepx}{$stepy}ifelse abs 2 mul setlinewidth}if newpath 0 1 $steps{pop $cyan $magenta $yellow $black setcmykcolor $fromx $fromy moveto $tox $toy lineto stroke /$fromx $fromx $stepx add def /$fromy $fromy $stepy sub def /$tox $tox $stepx add def /$toy $toy $stepy sub def /$cyan $cyan $cyanStep sub def /$magenta $magenta $magentaStep sub def /$yellow $yellow $yellowStep sub def /$black $black $blackStep sub def}for $isdouble{/$cyanStep $cyanStep neg def /$magentaStep $magentaStep neg def /$yellowStep $yellowStep neg def /$blackStep $blackStep neg def 0 1 $steps 1 sub{pop /$cyan $cyan $cyanStep sub def /$magenta $magenta $magentaStep sub def /$yellow $yellow $yellowStep sub def /$black $black $blackStep sub def $cyan $magenta $yellow $black setcmykcolor $fromx $fromy moveto $tox $toy lineto stroke /$fromx $fromx $stepx add def /$fromy $fromy $stepy sub def /$tox $tox $stepx add def /$toy $toy $stepy sub def}for}if grestore}bdef /myarc{90 exch sub exch 90 exch sub arc}bdef /arcfill{gsave 1 set'linewidth eoclip exch dup /$startangle xdef sub exch dup /$steps xdef div /$stepsize xdef /$hight xdef /$width xdef /$y xdef /$x xdef /$steps $steps 1 sub def dup /$black xdef exch sub $steps div /$blackStep xdef dup /$yellow xdef exch sub $steps div /$yellowStep xdef dup /$magenta xdef exch sub $steps div /$magentaStep xdef dup /$cyan xdef exch sub $steps div /$cyanStep xdef $x $y translate $hight $width gt{/$rad $width def 1 $hight $width div scale}{/$rad $hight def $width $hight div 1 scale} ifelse 1 -1 scale newpath 0 1 $steps{pop $cyan $magenta $yellow $black setcmykcolor 0 0 moveto 0 0 $rad $startangle dup $stepsize add dup /$startangle xdef myarc closepath eofill /$cyan $cyan $cyanStep sub def /$magenta $magenta $magentaStep sub def /$yellow $yellow $yellowStep sub def /$black $black $blackStep sub def}for grestore}bdef /DoGrayImage {/bpp exch def /sampv exch def /samph exch def /picstr samph string def translate scale{ 1 exch sub }settransfer samph sampv bpp [ samph 0 0 sampv 0 0 ]{ currentfile picstr readhexstring pop}image}bdef /DoColorImage {/nocolor systemdict /setcmykcolor known not def /bpp exch def /sampv exch def /samph exch def /comp1str samph string def /comp3str samph 3 mul string def translate scale /cvcomp1{/ii 0 def 0 3 comp3str length 3 idiv 3 mul{dup comp3str exch get exch dup 1 add comp3str exch get exch 2 add comp3str exch get .11 mul exch .59 mul add exch .3 mul add round cvi comp1str exch ii exch put /ii ii 1 add def}for}bdef samph sampv bpp [ samph 0 0 sampv 0 0 ] nocolor{{ currentfile comp3str readhexstring pop pop cvcomp1 comp1str }image }{{ currentfile comp3str readhexstring pop}false 3 colorimage } ifelse}bdef /buildfont{ exch findfont exch { dup length dict begin { 1 index /FID ne { def } { pop pop } ifelse } forall /Encoding NewCodes def currentdict end definefont } if [1 0 0 -1 0 0] makefont def }bdef /BeginEPSF { /b4_inc_state save def /dict_count countdictstack def /op_count count 1 sub def userdict begin /showpage { } def 0 setgray 0 setlinecap 1 setlinewidth 0 setlinejoin 10 setmiterlimit [] 0 setdash newpath /languagelevel where { pop languagelevel 1 ne { false setstrokeadjust false setoverprint } if } if } bind def /EndEPSF { count op_count sub { pop } repeat countdictstack dict_count sub { end } repeat b4_inc_state restore } bind def /currentpacking where{pop false setpacking}if end %%EndProcSet %%BeginSetup DeltaGraphPro begin 2 setmiterlimit n gsave clippath pathbbox /clipBot xdef /clipRight xdef /clipTop xdef /clipLeft xdef grestore clipRight clipLeft sub abs 589 abs div /xScale xdef clipBot clipTop sub abs 382 abs div /yScale xdef [ xScale 0 0 yScale 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C!C!C!C!C!C!C!C!C!C!C!C!C!C!C"C"C"C"C"C"C"C"C"C"C"C"C"C#C#C#C#C#C#C#C#C#C#C#C#C#C#C$C$C$C$C$C$C$C$C$C$C$C$C$C$C%C%C%C%C%C%C%C%C%C%C%C%C%C&C&C&C&C&C&C&C&C&C&C&C&C&C&C'C'C'C'C'C'C'C'C'C'C'C'C'C'C(C(C(C(C(C(C(C(C(C(C(C(C(C)C)C)C)C)C)C)C)C)C)C)C)C)C)C*C*C*C*C*C*C*C*C*C*C*C*C*C*C+C+C+C+C+C+C+C+C+C+C+C+C+C,C,C,C,C,C,C,C,C,C,C,C,C,C,C-C-C-C-C-C-C-C-C-C-C-C-C-C-C.C.C.C.C.C.C.C.C.C.C.C.C.C/C/C/C/C/C/C/C/C/C/C/C/C/C/C0C0C0C0C0C0C0C0C0C0C0C0C0C0C1C1C1C1C1C1C1C1C1C1C1C1C1C2C2C2C2C2C2C2C2C2C2C2C2C2C2C3C3C3C3C3C3C3C3C3C3C3C3C3C3C4C4C4C4C4C4C4C4C4C4C4C4C4C5C5C5C5C5C5C5C5C5C5C5C5C5C5C6C6C6C6C6C6C6C6C6C6C6C6C6C6C7C7C7C7C7C7C7C7C7C7C7C7C7C8C8C8C8C8C8C8C8C8C8C8C8C8C8C9C9C9C9C9C9C9C9C9C9C9C9C9C9C:C:C:C:C:C:C:C:C:C:C:C:C:C;C;C;C;C;C;C;C;C;C;C;C;C;C;C<C<C<C<C<C<C<C<C<C<C<C<C<C<C=C=C=C=C=C=C=C=C=C=C=C=C=C>C>C>C>C>C>C>C>C>C>C>C>C>C>C?C?C?C?C?C?C?C?C?C?C?C?C?C?C@C@C@C@C@C@C@C@C@C@C@C@C@CACACACACACACACACACACACACACACBCBCBCBCBCBCBCBCBCBCBCBCBCBCCCCCCCCCCCCCCCCCCCCCCCCCCCDCDCDCDCDCDCDCDCDCDCDCDCDCDCECECECECECECECECECECECECECECFCFCFCFCFCFCFCFCFCFCFCFCFCGCGCGCGCGCGCGCGCGCGCGCGCGCGCHCHCHCHCHCHCHCHCHCHCHCHCHCHCICICICICICICICICICICICICICJCJCJCJCJCJCJCJCJCJCJCJCJCJCKCKCKCKCKCKCKCKCKCKCKCKCKCKCLCLCLCLCLCLCLCLCLCLCLCLCLCMCMCMCMCMCMCMCMCMCMCMCMCMCMCNCNCNCNCNCNCNCNCNCNCNCNCNCNCOCOCOCOCOCOCOCOCOCOCOCOCOCPCPCPCPCPCPCPCPCPCPCPCPCPCPCQCQCQCQCQCQCQCQCQCQCQCQCQCQCRCRCRCRCRCRCRCRCRCRCRCRCRCSCSCSCSCSCSCSCSCSCSCSCSCSCSCTCTCTCTCTCTCTCTCTCTCTCTCTCTCUCUCUCUCUCUCUCUCUCUCUCUCUCVCVCVCVCVCVCVCVCVCVCVCVCVCVCWCWCWCWCWCWCWCWCWCWCWCWCWCWCXCXCXCXCXCXCXCXCXCXCXCXCXCYCYCYCYCYCYCYCYCYCYCYCYCYCYCZCZCZCZCZCZCZCZCZCZCZCZCZCZC[C[C[C[C[C[C[C[C[C[C[C[C[C\C\C\C\C\C\C\C\C\C\C\C\C\C\C]C]C]C]C]C]C]C]C]C]C]C]C]C]C^C^C^C^C^C^C^C^C^C^C^C^C^C_C_C_C_C_C_C_C_C_C_C_C_C_C_C`C`C`C`C`C`C`C`C`C`C`C`C`C`CaCaCaCaCaCaCaCaCaCaCaCaCaCbCbCbCbCbCbCbCbCbCbCbCbCbCbCcCcCcCcCcCcCcCcCcCcCcCcCcCcCdCdCdCdCdCdCdCdCdCdCdCdCdCeCeCeCeCeCeCeCeCeCeCeCeCeCeCfCfCfCfCfCfCfCfCfCfCfCfCfCfCgCgCgCgCgCgCgCgCgCgCgCgCgChChChChChChChChChChChChChChCiCiCiCiCiCiCiCiCiCiCiCiCiCiCjCjCjCjCjCjCjCjCjCjCjCjCjCkCkCkCkCkCkCkCkCkCkCkCkCkCkClClClClClClClClClClClClClClCmCmCmCmCmCmCmCmCmCmCmCmCmCnCnCnCnCnCnCnCnCnCnCnCnCnCnCoCoCoCoCoCoCoCoCoCoCoCoCoCoCpCpCpCpCpCpCpCpCpCpCpCpCpCqCqCqCqCqCqCqCqCqCqCqCqCqCqCrCrCrCrCrCrCrCrCrCrCrCrCrCrCsCsCsCsCsCsCsCsCsCsCsCsCsCtCtCtCtCtCtCtCtCtCtCtCtCtCtCuCuCuCuCuCuCuCuCuCuCuCuCuCvCvCvCvCvCvCvCvCvCvCwCwCwCwCwCwCwCwCwCxCxCxCxCxCxCxCxCxCxCyCyCyCyCyCyCyCyCyCyCyCyCyCzCzCzCzCzCzCzCzCzCzCzCzCzC{C{C{C{C{C{C{C{C{C{C{C{C{C{C|C|C|C|C|C|C|C|C|C|C|C|C|C|C}C}C}C}C}C}C}C}C}C}C}C}C}C~C~C~C~C~C~C~C~C~C~C~C~C~C~CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCBBBBBBBAAAAAAA@@@@@@?????>>>>>>=======<<<<<;;;;;:::::99999988888887777776666666655555554444443333333222222211111100000000////////........-------,,,,,,+++++******))))(((''''&&&%%%$$$###"""!!!!                                      !!!!"""###$$$%%%&&&''''((())))******+++++,,,,,------......./////////0000000000111111222222233333334444445555555666666677777888888999999:::::::;;;;;;<<<<<=======>>>>>>?????@@@@@@AAAAAAABBBBBBBCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC 6e (F0(}20(}40(}60(}80(Rv100(U0)0.2)%0.4)$0.6)$0.8))1) 1.2)$1.4)$1.6)$1.8)*2/  (=Total Ion Counts 6e``eu`0   8    `   ? ? `  0 ?  0+ߠTime (Minutes) A1nA,iHA;iNA6 dIH(TCH+3(T2Cl+HEtherqMUUMQUpMUUMQU"Q$qp"(l Figure 3.)5$ Total ion chromatograph for the CH+3(zCl and ether mixture.'%!PS-Adobe-2.0 EPSF-1.2 %%Creator: DeltaGraph Professional 3.0 %%Title: (BF3 Mass Spec Figure:Chart View) %%Creation 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string def /UseMacStroke false def /savestate{FillGray FillCyan FillMagenta FillYellow FillBlack FillMac UseMacFill StrokeGray StrokeCyan StrokeMagenta StrokeYellow StrokeBlack StrokeMac UseMacStroke}bdef /restorestate{/UseMacStroke xdef /StrokeMac xdef /StrokeBlack xdef /StrokeYellow xdef /StrokeMagenta xdef /StrokeCyan xdef /StrokeGray xdef /UseMacFill xdef /FillMac xdef /FillBlack xdef /FillYellow xdef /FillMagenta xdef /FillCyan xdef /FillGray xdef}bdef /cmyk{/FillBlack xdef /FillYellow xdef/FillMagenta xdef/FillCyan xdef}bdef /CMYK{/StrokeBlack xdef /StrokeYellow xdef/StrokeMagenta xdef/StrokeCyan xdef}bdef /apat 8 string def/mat matrix def 1 0 mat defaultmatrix dtransform exch atan/patang xdef /sscrn{currentscreen/proc xdef/ang xdef/freq xdef}bdef /rscrn{freq ang/proc load setscreen}bdef /macpat{apat copy pop 9.375 patang {1 add 4 mul cvi apat exch get exch 1 add 4 mul cvi 7 sub bitshift 1 and}setscreen setgray}bdef /d/setdash ldef /g{false/UseMacFill xdef/FillGray xdef}bdef /mg{true/UseMacFill xdef FillMac copy pop/FillGray xdef}bdef /G{false/UseMacStroke xdef/StrokeGray xdef}bdef /MG{true/UseMacStroke xdef StrokeMac copy pop/StrokeGray xdef}bdef /_i currentflat def /i{dup 0 eq{pop _i}if setflat}bdef /j/setlinejoin ldef /J/setlinecap ldef /M/setmiterlimit ldef /w/setlinewidth ldef /_R{.25 sub round .25 add}bdef /_r{transform _R exch _R exch itransform}bdef /m{_r moveto}bdef /L{_r lineto}bdef /c{_r curveto}bdef /_gf{1.0 FillGray sub mul}bdef /_gs{1.0 StrokeGray sub mul}bdef /sf{UseMacFill{FillCyan FillMagenta FillYellow FillBlack setcmykcolor sscrn FillGray FillMac macpat}{FillGray setgray FillCyan _gf FillMagenta _gf FillYellow _gf FillBlack _gf setcmykcolor}ifelse}bdef /ss{UseMacStroke{StrokeCyan StrokeMagenta StrokeYellow StrokeBlack setcmykcolor sscrn StrokeGray StrokeMac macpat}{StrokeGray setgray StrokeCyan _gs StrokeMagenta _gs StrokeYellow _gs StrokeBlack _gs setcmykcolor}ifelse}bdef /F{sf eofill UseMacFill{rscrn}if}bdef /f{closepath F}bdef /S{ss stroke UseMacStroke{rscrn}if}bdef /s{closepath S}bdef /B{gsave F grestore S}bdef /b{closepath B}bdef /N/newpath ldef /n/N ldef /sh{currentpoint 3 -1 roll show 3 -1 roll add moveto}bdef /NewCodes 256 array def /NUL/SOH/STX/ETX/EOT/ENQ/ACK/BEL/BS/HT/LF/VT/FF/CR/SO/SI /DLE/DC1/DC2/DC3/DC4/NAK/SYN/ETB/CAN/EM/SUB/ESC/FS/GS/RS/US NewCodes 0 32 getinterval astore pop NewCodes 32/Times-Roman findfont/Encoding get 32 96 getinterval putinterval NewCodes dup 39/quotesingle put 96/grave put /Adieresis/Aring/Ccedilla/Eacute/Ntilde/Odieresis/Udieresis/aacute /agrave/acircumflex/adieresis/atilde/aring/ccedilla/eacute/egrave /ecircumflex/edieresis/iacute/igrave/icircumflex/idieresis/ntilde/oacute /ograve/ocircumflex/odieresis/otilde/uacute/ugrave/ucircumflex/udieresis /dagger/degree/cent/sterling/section/bullet/paragraph/germandbls /registered/copyright/trademark/acute/dieresis/notequal/AE/Oslash /infinity/plusminus/lessequal/greaterequal/yen/mu/partialdiff/summation /product/pi/integral/ordfeminine/ordmasculine/Omega/ae/oslash /questiondown/exclamdown/logicalnot/radical/florin/approxequal/Delta/guillemotleft /guillemotright/ellipsis/blank/Agrave/Atilde/Otilde/OE/oe /endash/emdash/quotedblleft/quotedblright/quoteleft/quoteright/divide/lozenge /ydieresis/Ydieresis/fraction/currency/guilsinglleft/guilsinglright/fi/fl /daggerdbl/periodcentered/quotesinglbase/quotedblbase/perthousand/Acircumflex /Ecircumflex/Aacute /Edieresis/Egrave/Iacute/Icircumflex/Idieresis/Igrave/Oacute/Ocircumflex /apple/Ograve/Uacute/Ucircumflex/Ugrave/dotlessi/circumflex/tilde /macron/breve/dotaccent/ring/cedilla/hungarumlaut/ogonek/caron NewCodes 128 128 getinterval astore pop /oshow{/str2 xdef .1 w 0 1 str2 length 1 sub{str2 exch 1 getinterval false charpath currentpoint stroke m}for}bdef /ktx{newpath /$1 xdef /$2 xdef /$3 xdef /$4 xdef $3 $2 moveto $4 show $1 0 gt{$1 2 div w 0 $1 rmoveto $3 $2 $1 add lineto stroke}if}bdef /tx{newpath /$1 xdef /$2 xdef /$3 xdef /$4 xdef dup /$5 xdef 0 1 $4 length 1 sub{$4 exch 1 getinterval exch $2 moveto $3}for $1 0 gt{$1 2 div w 0 $1 rmoveto $5 $2 $1 add lineto stroke}if}bdef /stx{newpath /$1 xdef /$2 xdef /$3 xdef /$4 xdef dup /$5 xdef 0 1 $4 length 1 sub{$4 exch 1 getinterval exch dup SYM eq{pop exch $2 moveto currentfont SymbolFont setfont exch $3 setfont}{$2 moveto $3}ifelse}for}bdef /showsym{moveto gsave /ch xdef currentpoint initmatrix translate 0 0 moveto currentfont /FontName get /Courier eq ch exch charpath flattenpath pathbbox /ury xdef /urx xdef /lly xdef /llx xdef urx llx sub -2 div llx sub ury lly sub -2 div lly sub grestore rmoveto ch show}def /ps2mac{1 -1 scale neg 0 exch translate}bdef /mac2ps{0 exch translate 1 -1 scale}bdef /xpat{gsave setcmykcolor eofill grestore gsave FillCyan FillMagenta FillYellow FillBlack setcmykcolor eoclip /thepat xdef /right xdef/bottom xdef/left xdef/top xdef /sizev xdef /sizeh xdef /shrink exch 72 div def /howmanywide left right sub abs cvi sizeh idiv 1 add shrink mul 1 add cvi def /howmanydown bottom top sub abs cvi sizev idiv 1 add shrink mul 1 add cvi def left top translate sizeh shrink div sizev shrink div scale howmanydown{gsave howmanywide{sizeh sizev true [sizeh 0 0 sizev 0 0]{thepat}imagemask 1 0 translate}repeat grestore 0 1 translate}repeat grestore}bdef /drawrect{/$r xdef /$b xdef /$l xdef /$t xdef $l $t m $r $t L $r $b L $l $b L closepath}bdef /drawdiamond{/$r xdef /$b xdef /$l xdef /$t xdef $l $r add 2 div $t m $l $t $b add 2 div L $l $r add 2 div $b L $r $t $b add 2 div L closepath}bdef /ellipse{newpath/savematrix matrix currentmatrix def translate scale 0 0 1 5 -2 roll arc savematrix setmatrix}bdef /drawcircle{/$r xdef /$b xdef /$l xdef /$t xdef 0 360 $r $l sub 2 div $t $b sub 2 div $r $l add 2 div $b $t add 2 div ellipse}bdef /dofill{gsave 1 setlinewidth eoclip /$drawit xdef /$steps xdef /$cv xdef /$ch xdef /$r xdef /$b xdef /$l xdef /$t xdef /$tstep $t $cv sub $steps div def /$bstep $b $cv sub $steps div def /$lstep $l $ch sub $steps div def /$rstep $r $ch sub $steps div def dup /$black xdef exch sub $steps div /$blackStep xdef dup /$yellow xdef exch sub $steps div /$yellowStep xdef dup /$magenta xdef exch sub $steps div /$magentaStep xdef dup /$cyan xdef exch sub $steps div /$cyanStep xdef newpath 0 1 $steps{pop $cyan $magenta $yellow $black setcmykcolor $t $l $b $r $drawit eofill /$t $t $tstep sub def /$l $l $lstep sub def /$b $b $bstep sub def /$r $r $rstep sub def /$cyan $cyan $cyanStep sub def /$magenta $magenta $magentaStep sub def /$yellow $yellow $yellowStep sub def /$black $black $blackStep sub def}for grestore}bdef /dolfill{gsave 1 setlinewidth eoclip 1 sub /$steps xdef /$r xdef /$b xdef /$l xdef /$t xdef /$type xdef 1 eq /$isdouble xdef dup /$black xdef exch sub $steps div /$blackStep xdef dup /$yellow xdef exch sub $steps div /$yellowStep xdef dup /$magenta xdef exch sub $steps div /$magentaStep xdef dup /$cyan xdef exch sub $steps div /$cyanStep xdef $type 1 eq{/$fromx $l def /$fromy $t def /$tox $r def /$toy $t def /$stepx 0 def /$stepy $t $b sub $steps div $isdouble{2 div}if def $stepx abs $stepy abs gt{$stepx}{$stepy}ifelse abs setlinewidth}if $type 2 eq{/$fromx $l def /$fromy $t def /$tox $l def /$toy $b def /$stepx $r $l sub $steps div $isdouble{2 div}if def /$stepy 0 def $stepx abs $stepy abs gt{$stepx}{$stepy}ifelse abs setlinewidth}if $type 3 eq{/$fromx $l $r $l sub 2 div sub def /$fromy $t $b add 2 div def /$tox $r $l add 2 div def /$toy $t $t $b sub 2 div add def /$stepx $r $l sub $steps div $isdouble{2 div}if def /$stepy $t $b sub $steps div $isdouble{2 div}if def $stepx abs $stepy abs gt{$stepx}{$stepy}ifelse abs 2 mul setlinewidth}if $type 4 eq{/$fromx $r $r $l sub 2 div add def /$fromy $t $b add 2 div def /$tox $r $l add 2 div def /$toy $t $t $b sub 2 div add def /$stepx $r $l sub $steps div neg $isdouble{2 div}if def /$stepy $t $b sub $steps div $isdouble{2 div}if def $stepx abs $stepy abs gt{$stepx}{$stepy}ifelse abs 2 mul setlinewidth}if newpath 0 1 $steps{pop $cyan $magenta $yellow $black setcmykcolor $fromx $fromy moveto $tox $toy lineto stroke /$fromx $fromx $stepx add def /$fromy $fromy $stepy sub def /$tox $tox $stepx add def /$toy $toy $stepy sub def /$cyan $cyan $cyanStep sub def /$magenta $magenta $magentaStep sub def /$yellow $yellow $yellowStep sub def /$black $black $blackStep sub def}for $isdouble{/$cyanStep $cyanStep neg def /$magentaStep $magentaStep neg def /$yellowStep $yellowStep neg def /$blackStep $blackStep neg def 0 1 $steps 1 sub{pop /$cyan $cyan $cyanStep sub def /$magenta $magenta $magentaStep sub def /$yellow $yellow $yellowStep sub def /$black $black $blackStep sub def $cyan $magenta $yellow $black setcmykcolor $fromx $fromy moveto $tox $toy lineto stroke /$fromx $fromx $stepx add def /$fromy $fromy $stepy sub def /$tox $tox $stepx add def /$toy $toy $stepy sub def}for}if grestore}bdef /myarc{90 exch sub exch 90 exch sub arc}bdef /arcfill{gsave 1 se'tlinewidth eoclip exch dup /$startangle xdef sub exch dup /$steps xdef div /$stepsize xdef /$hight xdef /$width xdef /$y xdef /$x xdef /$steps $steps 1 sub def dup /$black xdef exch sub $steps div /$blackStep xdef dup /$yellow xdef exch sub $steps div /$yellowStep xdef dup /$magenta xdef exch sub $steps div /$magentaStep xdef dup /$cyan xdef exch sub $steps div /$cyanStep xdef $x $y translate $hight $width gt{/$rad $width def 1 $hight $width div scale}{/$rad $hight def $width $hight div 1 scale} ifelse 1 -1 scale newpath 0 1 $steps{pop $cyan $magenta $yellow $black setcmykcolor 0 0 moveto 0 0 $rad $startangle dup $stepsize add dup /$startangle xdef myarc closepath eofill /$cyan $cyan $cyanStep sub def /$magenta $magenta $magentaStep sub def /$yellow $yellow $yellowStep sub def /$black $black $blackStep sub def}for grestore}bdef /DoGrayImage {/bpp exch def /sampv exch def /samph exch def /picstr samph string def translate scale{ 1 exch sub }settransfer samph sampv bpp [ samph 0 0 sampv 0 0 ]{ currentfile picstr readhexstring pop}image}bdef /DoColorImage {/nocolor systemdict /setcmykcolor known not def /bpp exch def /sampv exch def /samph exch def /comp1str samph string def /comp3str samph 3 mul string def translate scale /cvcomp1{/ii 0 def 0 3 comp3str length 3 idiv 3 mul{dup comp3str exch get exch dup 1 add comp3str exch get exch 2 add comp3str exch get .11 mul exch .59 mul add exch .3 mul add round cvi comp1str exch ii exch put /ii ii 1 add def}for}bdef samph sampv bpp [ samph 0 0 sampv 0 0 ] nocolor{{ currentfile comp3str readhexstring pop pop cvcomp1 comp1str }image }{{ currentfile comp3str readhexstring pop}false 3 colorimage } ifelse}bdef /buildfont{ exch findfont exch { dup length dict begin { 1 index /FID ne { def } { pop pop } ifelse } forall /Encoding NewCodes def currentdict end definefont } if [1 0 0 -1 0 0] makefont def }bdef /BeginEPSF { /b4_inc_state save def /dict_count countdictstack def /op_count count 1 sub def userdict begin /showpage { } def 0 setgray 0 setlinecap 1 setlinewidth 0 setlinejoin 10 setmiterlimit [] 0 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p l cp SM lW 0.8 m sl st gr}{P}{4 2 r gs OP/rad x 1 SA DA gr}{P}}o 1 g 1 s g e 2 4 gi al P 5 -1 r xc}{al P 8 ix 1 eq{DD}{DS}ie 5 -1 r 2 eq{DB}{DS}ie P}{DT}}o 0 g g xc}b /SP{/sf x/lW x/bW x/cW x SPn}b/SPn{gs count 9 ge 7 ix 192837465 eq and{7 -1 r P 6 -2 r o o xl 7 -1 r s e 7 -1 r s e 5 -1 r dv neg e 5 -1 r dv neg e sc neg e neg e xl}{xl P P}ie 1 1 S dv D sc CMT currentmatrix P lW sl 4.0 setmiterlimit np}b "q""v"v""""&"3""""end %%EndProcSet 40 80 20 20 54 chemdict30 begin/hS x/sf x/lW x/bW x/cW x/sh T d 383 101 66 143 SPn/origstk x 65535 65535 65535 sBg 0 0 0 C np 2250 3600 M 2250 3620 l 1860 3620 l 1860 3600 l cp f np 2970 3600 M 2970 3620 l 2490 3620 l 2490 3600 l cp f np 2360 3160 M 2380 3160 l 2380 3470 l 2360 3470 l cp f np 2380 4060 M 2360 4060 l 2360 3750 l 2380 3750 l cp f np 3580 3600 M 3580 3620 l 3110 3620 l 3110 3600 l cp f np 5660 3130 M 5680 3130 l 5680 3450 l 5660 3450 l cp f np 5295 3818 M 5285 3800 l 5545 3650 l 5555 3668 l cp f np 5889 3948 M 5871 3958 l 5736 3726 l 5754 3716 l cp f np 6140 3580 M 6140 3600 l 5790 3600 l 5790 3580 l cp f np 8060 3170 M 8080 3170 l 8080 3490 l 8060 3490 l cp f np 7695 3858 M 7685 3840 l 7945 3690 l 7955 3708 l cp f np 8289 3988 M 8271 3998 l 8136 3766 l 8154 3756 l cp f np 8560 3620 M 8560 3640 l 8190 3640 l 8190 3620 l cp f gr count origstk sub{P}rp end chemsave restore ,Times .+DH @+ 3 @(SC) C(sCH +3 (sCH +3 (O(CH +3 (Mtert-butylmethyl ether (C(H(H+) H(6Cl+ZC(H(uH+) H(Br ( chloromethane+ BromomethanedDCHMDSTRGB x (XP6$$ L$  L| L$ 0 $ 0 0<(\8! "d$@ &8!(     # % ' )CH3CCH3CH3CH3CH H H Cl C HHHBr    DO `8 8 ` 0 h l  `  `_ P `     8tert-butylmethyl ether `t t `  T  ` `| | `t8 8t( `@* @ ` D6+ |@ D `.,8 ` b- l!  `!. !" m / chloromethane  80 8" BromomethaneTimesc 175.16 323.016 176.168 322.871 177.18 323.027 c 178.188 323.18 179.191 325.172 180.203 323.027 c 181.211 320.879 182.219 315.391 183.23 310.805 c 184.238 306.215 185.246 302.531 186.258 298.586 c 187.266 294.637 188.27 290.32 189.281 286.367 c 190.289 282.41 191.297 280.379 192.309 274.148 c 193.316 267.914 194.32 258.066 195.332 249.711 c 196.34 241.352 197.348 237.574 198.359 225.273 c 199.367 212.969 200.375 193.672 201.387 176.398 c 202.395 159.121 203.398 144.758 204.4Uirs-.  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