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231224s2013 xx |||||o 00| ||eng c |
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|a 10.1002/mrc.3951
|2 doi
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|a pubmed24n0754.xml
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|a eng
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|a Afonin, Andrei V
|e verfasserin
|4 aut
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|a Structural peculiarities of configurational isomers of 1-styrylpyrroles according to 1Н, 13С and 15N NMR spectroscopy and density functional theory calculations
|b electronic and steric hindrance for planar structure
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|c 2013
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|a Text
|b txt
|2 rdacontent
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|a ƒaComputermedien
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|2 rdamedia
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|a ƒa Online-Ressource
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|a Date Completed 16.05.2014
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|a Date Revised 16.05.2013
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|a published: Print-Electronic
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|a Citation Status MEDLINE
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|a Copyright © 2013 John Wiley & Sons, Ltd.
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|a Comparative analysis of the (1)Н and (13)С NMR data for a series of the E and Z-1-styrylpyrroles, E and Z-1-(1-propenyl)pyrroles, 1-vinylpyrroles and styrene suggests that the conjugation between the unsaturated fragments in the former compounds is reduced. This is the result of the mutual influence of the donor p-π and π-π conjugation having opposite directions. According to the NMR data combined with the density functional theory calculations, the Z isomer of 1-styrylpyrrole has essentially a nonplanar structure because of the steric hindrance. However, the E isomer of 1-styrylpyrrole is also an out-of-plane structure despite the absence of a sterical barrier for the planar one. Deviation of the E isomer from the planar structure seems to be caused by an electronic hindrance produced by a mutual influence of the p-π and π-π conjugation. The structure of the E isomer of the 2-substituted 1-styrylpyrroles is similar to that of the 2-substituted 1-vinylpyrroles. The steric effects in the Z isomer of the 2-substituted 1-styrylpyrroles result in the large increase of the dihedral angle between planes of the pyrrole ring and double bond
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|a Journal Article
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|a Research Support, Non-U.S. Gov't
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|a Carbon Isotopes
|2 NLM
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|a Nitrogen Isotopes
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|a Protons
|2 NLM
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|a Pyrroles
|2 NLM
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|a Ushakov, Igor A
|e verfasserin
|4 aut
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|a Pavlov, Dmitry V
|e verfasserin
|4 aut
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|a Schmidt, Elena Yu
|e verfasserin
|4 aut
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|a Dvorko, Marina Yu
|e verfasserin
|4 aut
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|i Enthalten in
|t Magnetic resonance in chemistry : MRC
|d 1985
|g 51(2013), 6 vom: 07. Juni, Seite 339-49
|w (DE-627)NLM098179667
|x 1097-458X
|7 nnns
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|g volume:51
|g year:2013
|g number:6
|g day:07
|g month:06
|g pages:339-49
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|u http://dx.doi.org/10.1002/mrc.3951
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