The Styrene Probe Applied to 15N and 77Se NMR

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Abstract:

Previous work had shown that the Fluorine 19 NMR chemical shift deltaHammett Substituent Constant sigma correlation of ethyl alpha- fluorocinnamates gave a positive slope greater deshielding with increasing sigma value, opposite to that predicted by the pi-polarization mechanism. To ascertain if this was a general phenomenon in alpha-substituted cinnamate esters for atoms having unshared pairs of electrons, Nitrogen 15 chemical shift correlations were obtained for the Z and E isomers of ethyl alpha- diethylaminocinnamates Series A, 13 compounds. A positive slope was found for both isomers, with the sigma- scale giving the best single substituent parameter result compared to sigma, sigma, and sigma 13, indicating through- resonance to be predominant in these compounds. This correlation study was extended to a series of benzylidene azlactones Series B, 10 compounds and ethyl alpha-cyanocinnamates Series C, 7 compounds. Selenium 77 NMR of the E and Z isomers of ethyl alpha-phenylseleno-cinnamates Series D also revealed a positive slope, although there was a large isomer disparity in correlative behavior. Theses. aw

Author(s):
Shaffer, Alan A.
Author Organization(s):
AIR FORCE INST OF TECH WRIGHT-PATTERSON AFB OH
Descriptive Note:
Doctoral thesis,
Pagination:
0349

Security Markings

DOCUMENT & CONTEXTUAL SUMMARY

Distribution:
Approved For Public Release
Distribution Statement:
Approved For Public Release; Distribution Is Unlimited.

RECORD

Collection: TR
Identifying Numbers
Report Number(s):
AFIT/CI/CIA-88-225
Monitor Series:
AFIT
 Subject Terms
Joint Capability Areas:
JCA_8_Building Partnerships; JCA_8.1_Communicate; JCA_5_Command and Control; JCA_8.1.3_Influence Adversary and Competitor Audiences; JCA_5.3_Planning; JCA_8.1.1_Inform Domestic and Foreign Audiences; JCA_6.3.3_Spectrum Management; JCA_6_Net Centric; JCA_1_Force Support; JCA_6.3_Net Management; JCA_1.2_Force Preparation; JCA_3.2_Engagement; JCA_3_Force Application; JCA_6.1_Information Transport; JCA_3.2.1_Kinetic Means; JCA_1.2.5_Lessons Learned; JCA_1.2.3_Educating; JCA_1.2.6_Concepts; JCA_1.3_Human Capital Management; JCA_1.3.2_Personnel Management; JCA_1.2.7_Experimentation
Modernization Areas:
Microelectronics
Communities of Interest:
Energy and Power Technologies
Descriptor(s):
*NUCLEAR MAGNETIC RESONANCE, *CINNAMIC ACID, *CHEMICAL SHIFTS, *ESTERS, *ISOMERS, *SPECTROSCOPY, ATOMS, PROBES, BENZYL RADICALS, AMINES, ELECTRONS, CORRELATION, FLUORINE, SLOPE, SELENIUM, THESES, STYRENES, PARAMETERS, ETHYL RADICALS, LACTONES, NITROGEN
Field(s)/Group(s):
Organic Chemistry, Physical Chemistry
Keyword(s):
*CINNAMATES, FLUOROCINNAMATES, CINNAMATE ESTERS, DIETHYLAMINOCINNAMATES, BENZYLIDENES, PHENYLSELENOCINNAMATES, NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY
Report Date:
1988 Aug 01