NDLI: DFT study of 1-, 4-, and 5-substituted 2-oxo-1,2,3,4-tetrahydropyrimidines: substituent steric and electronic effects, and ring flipping

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DFT study of 1-, 4-, and 5-substituted 2-oxo-1,2,3,4-tetrahydropyrimidines: substituent steric and electronic effects, and ring flipping

Content Provider	Springer Nature Link
Author	Memarian, Hamid R. Sabzyan, Hassan Ranjbar, Mahnaz
Copyright Year	2013
Abstract	Steric and the electronic effects caused by the substituents in the 1-, 4-, and 5-positions of substituted 2-oxo-1,2,3,4-tetrahydropyrimidines were investigated using density functional theory at the B3LYP/6-31++G(d,p) level. Results of this study show that the heterocyclic ring adopts a pseudo-boat conformation, in which the C$_{4}$ and N$_{1}$ atoms are deviated from ring planarity. The C$_{4}$-substituent occupies a pseudo-axial position and the space orientation of the substituent depends on the type and position of the additional substituent in this aryl group. The heights of the C$_{4}$ and N$_{1}$ atoms from the boat plane and the orientation of 5-CO moiety toward the heterocyclic ring depend on the electronic and steric effects of the substituents in the various positions. Ring flip calculations for 4-phenyl substituent explain the extreme steric effect caused by the substituent in the 1-position. These calculations indicate the more favored pseudo-axial orientation of the phenyl group over the equatorial orientation.
Starting Page	85
Ending Page	94
Page Count	10
File Format	PDF
ISSN	10400400
Journal	Structural Chemistry
Volume Number	25
Issue Number	1
e-ISSN	15729001
Language	English
Publisher	Springer US
Publisher Date	2013-03-24
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	B3LYP/6-31++G(d,p) Ring flip Steric hindrance Substituent effect Tetrahydropyrimidines Computer Applications in Chemistry Physical Chemistry Theoretical and Computational Chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Condensed Matter Physics

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