Determination of Dipole Moments of Selected Organic Compounds

142 Pages·07.967 MB·English

by  Myers, Albert Leroy

PURDUE UNIVERSITY
THIS IS TO CERTIFY THAT THE THESIS PREPARED UNDER MY SUPERVISION
BY______..Albert .Leroy Myers
P’RT'SRH/'INATIOI’J OF DIPOLE MOMENTS OF SELECTED
entitled
ORGANIC_COMPOUND!.
COMPLIES WITH THE UNIVERSITY REGULATIONS ON GRADUATION THESES
AND IS APPROVED BY ME AS FULFILLING THIS PART OF THE REQUIREMENTS
FOR THE DEGREE OF
-Doctor .of Philosophy.
Professor in Charge of Thesis
Hear of School or Department
TO THE LIBRARIAN:-----
1S,
THIS THESIS IS NOT TO BE REGARDED AS CONFIDENTIAL.
. lie.
PKOFESSOH HT CHABGE
GRAD. SCHOOL FORM 9—3-49—1M

DETERMINATION OP DIPOLE MOMENTS OP
SELECTED ORGANIC COMPOUNDS
A Thesis
Submitted to the Faculty
of
Purdue University
by
Albert Leroy Myers
In Partial Fulfillment of the:
Requirements for the Degree
of
Doctor of Philosophy
June, 1950
ProQuest Number: 27714115
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AC KNOWLEDGMEOT
The author wishes to express his
sincere appreciation to Professor Thomas
DeVries, who directed this work, for his
helpful suggestions throughout the re­
search and the preparation of this paper.
The author also wishes to thank the
Purdue Research Foundation, which financed
this research through a Research Fellow­
ship .
TABLE OF CONTENTS
Page
ABSTRACT........... i
INTRODUCTION.............. 1
EXPERIMENTAL.......................................... 17
Apparatus ........................ 17
Procedure...................... 26
Calculations.................... 30
Materials....... 38
RESULTS............................................... 41
Aliphatic Nitro Compounds................ 4$"
Organic Silicon Compounds................ 86
Fluorine Derivatives of Benzene.......... 88
Halogen Derivatives of Trifluoromethylbenzene....... 89
Halogen Derivatives of Benzene with Two Trifluoro-
methyl Groups............ .................. 91
Pentafluoroethyl Derivatives of Benzene...... 92
Ether Derivatives of Trifluoromethylbenzene. ..... 94
Ether Derivatives of Benzene with Two Trifluoro-
methyl Groups.................. 97
DISCUSSION. .... 100
SUMMARY............................................... 108
BIBLIOGRAPHY.......................................... 109
VITA......................................... ........
TABLES
Table PaS©
1. 2-Nitrophenylt rimethyls liane...................... 31
2m Physical Constants............ 39
3. Molar Refractivities............... 42
4. Nitroethane in Benzene at 25^................. . 46
5* 1-Nitropropane in Benzene at 25°• • ........... 47
6. 2-Nitropropane in Benzene at 25°............. 48
7. 1,1-Dinitroethane in Benzene at 25°• •. »........... 49
8. TrimethyIpheny1si1ane in Benzene at 25°•...... 50
9* Trimethylbenzylsilane in Benzene at 25°........... 51
10. Triethylphenylsilane in Benzene at 25°....... . 52
11. 2-Nitrophenyltrimethylsilane in Benzene at 25°. • • « • 53
12. Fluorobenzene in Benzene at 25°................... 54
13* 4-Fluorotoluene in Benzene at 25°................. 55
14. 4-Ghlorotrifluoroinethylbenzene in Benzene at 25°. • * 56
15. 2-Chlorotrifluoromethylbenzene in Benzene at 25°. • • 57
16. 3,4-Dichlorotrifluoromethylbenzene in Benzene at
25°............................ 58
17• 2-Bromo-5-ohlorotrifluoromethylbenzene in
Benzene at 25°.................. 59
18. 2-0hloro-5whromotrifluoromethylbenzene in
Benzene at 25 0................ *................ 60
19. 5-Bromo-2,4-dichlorotrifluoroniethylbenzene in
Benzene at 25°................................. 61
20. 3-Bromo-4,5-dichlorotrifluoromethylbenzene in
Benzene at 25°........................ 62
21. 5-0hloro-l,3-his (trifluoroniethyl)benzene in
Benzene at 250................................. 63
TABLES (Cont.)
Table PaSe
22. 4-Chloro-l,3-bis(trifluoromethyl)benzene
in Benzene at 25°... ^
23. 4,5-Diohloro-l»2-bis(trifluorometbyl)benzene
in Benzene at 25°..................*........... ^5
24. 4,3-Dictiloro-l, 3-bis ( trif luoromethyl ) benzene
in Benzene at 25° 66
25. 4,5,6-Trichloro-l,3-bis(trifluoromethyl)benzene
in Benzene at 25°......... 67
26. 2,3>5-Trichloro-l,4-bis(trifluoromethyl)benzene
in Benzene at 25° .................... 68
27. 3-Ghloropentafluoroethylbenzene in Benzene at 25° • • 69
28. 5-Ghloro-l, 3-bis ( pentafluoroethyl )benzene
in Benzene at 25° ................. 70
29. 2,5-Dichloro-4-trifluoromethylpentafluoroethyl-
benzene in Benzene at 25°. ............. 71
30. 4-Hethoxytrifluoromethylbenzene in Benzene at 25°•• 72
31. 4-Ethoxytrifluoromethylbenzene in Benzene at 25°••• 73
32. 4-Isopropoxytrifluoromethylbenzene in
Benzene at 25°............ 74
33* 2-Isopropoxytrifluoromethylbenzene in
Benzene at 25°.... ............................ 75
34. 2-Methoxy-l,4-bis(trifluoromethyl)benzene in
Benzene at 25°....... 76
35* 2-Methoxy-l, 3-bis (trif luoromethyl )benzene in
Benzene at 25°..................... 77
36. 5-Methoxy-l,3-bis(trifluoromethyl)benzene in
Benzene at 25°.... .......... ................ 78
37* 5-Sthoxy-l,3-bis(trifluoromethyl)benzene in
Benzene at 25°..................... 79
38. . 5-Butoxy-l,3-bis(trifluoromethyl)benzene in
Benzene at 25°................................ 80
TABLES (Cont.)
Tables Page
39- 4-Methoxy-l,3-bis(trifluoromethyl)benzene
in Benzene at 25°...............*.............. 81
40. 4-Ethoxy-l,3-bis(trifluoromethyl)benzene
in Benzene at 25°..................... 82
41. 4-Propoxy-l,3-bis (trifluoromethyl )benzene
in Benzene at 25° ...... .. ..... 83
42. 4-1sopropoxy-1,3-b i s(tri fluo romethyl)benzene
in Benzene at 25°. ............................ 84
43. 4-Phenoxy-l ,3-bis (trif luoromethyl )benzene
in Benzene at 25°*........*......... 85
44. Experimental Data for the Hedestrand and
Guggenheim Equations ..... 101
45. Dipole Moments in Benzene Solution................ 103
FIGURES
Figure Page
1. Bridge, Resonance and Heterodyne Beat
Apparatus ..... 14
2. Plate Assembly..... 19
3* Plate Assembly Container andM ixing Chamber....... 20
4. Oscillator Block Diagram................... . 23
5. Oscillator Circuit Diagram........... ........... 25
6. 2-Nitrophenyltrimethylsilane in Benzene
(D vs. fg).................. .................. 34