Saturated heterocycles, 68. Application of the Seth-Paul-Van Duyse equation, IX - The C=O stretching frequencies and substituent effects in 5,6-polymethylenepyrimidin-4(3 H)-one derivatives

Alexander Perjéssy, János Lázár, G. Bernáth

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4 Citations (Scopus)

Abstract

The C=O stretching frequencies of 32 5,6-polymethylenepyrimidin-4(3H)-one (1a-1w) and cis-5,6-polymethylene-5,6-dihydropyrimidin-4(3 H)-one (2a-2h) derivatives were measured in tetrachlormethane and in chloroform and correlated with the substituent constants X+ (R) in the sense of the modified and extended Seth-Paul-Van Duyse equation. It was found that the C=O stretching frequency and the transmission of substituent effects through the heterocyclic ring are significantly influenced by the size of the fused hydrocarbon ring. Evidence was obtained that in molecules linked by intermolecular hydrogen bonds the substituent effects are transmitted to the C=O group predominantly via the C=N-C=C part of the pyrimidinone ring. In the free molecules the transmission of substituent effects takes place mainly through the NH group.

Original languageEnglish
Pages (from-to)97-104
Number of pages8
JournalMonatshefte fur Chemie
Volume117
Issue number1
DOIs
Publication statusPublished - Jan 1986

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Stretching
Pyrimidinones
Derivatives
Molecules
Chloroform
Hydrocarbons
Hydrogen bonds

Keywords

  • 5,6-Polymetylenepyrimidin-4(3H)-ones
  • C=O Stretching frequencies
  • Seth-Paul-Van Duyse equation
  • Substituent effects

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Saturated heterocycles, 68. Application of the Seth-Paul-Van Duyse equation, IX - The C=O stretching frequencies and substituent effects in 5,6-polymethylenepyrimidin-4(3 H)-one derivatives",
abstract = "The C=O stretching frequencies of 32 5,6-polymethylenepyrimidin-4(3H)-one (1a-1w) and cis-5,6-polymethylene-5,6-dihydropyrimidin-4(3 H)-one (2a-2h) derivatives were measured in tetrachlormethane and in chloroform and correlated with the substituent constants X+ (R) in the sense of the modified and extended Seth-Paul-Van Duyse equation. It was found that the C=O stretching frequency and the transmission of substituent effects through the heterocyclic ring are significantly influenced by the size of the fused hydrocarbon ring. Evidence was obtained that in molecules linked by intermolecular hydrogen bonds the substituent effects are transmitted to the C=O group predominantly via the C=N-C=C part of the pyrimidinone ring. In the free molecules the transmission of substituent effects takes place mainly through the NH group.",
keywords = "5,6-Polymetylenepyrimidin-4(3H)-ones, C=O Stretching frequencies, Seth-Paul-Van Duyse equation, Substituent effects",
author = "Alexander Perj{\'e}ssy and J{\'a}nos L{\'a}z{\'a}r and G. Bern{\'a}th",
year = "1986",
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T1 - Saturated heterocycles, 68. Application of the Seth-Paul-Van Duyse equation, IX - The C=O stretching frequencies and substituent effects in 5,6-polymethylenepyrimidin-4(3 H)-one derivatives

AU - Perjéssy, Alexander

AU - Lázár, János

AU - Bernáth, G.

PY - 1986/1

Y1 - 1986/1

N2 - The C=O stretching frequencies of 32 5,6-polymethylenepyrimidin-4(3H)-one (1a-1w) and cis-5,6-polymethylene-5,6-dihydropyrimidin-4(3 H)-one (2a-2h) derivatives were measured in tetrachlormethane and in chloroform and correlated with the substituent constants X+ (R) in the sense of the modified and extended Seth-Paul-Van Duyse equation. It was found that the C=O stretching frequency and the transmission of substituent effects through the heterocyclic ring are significantly influenced by the size of the fused hydrocarbon ring. Evidence was obtained that in molecules linked by intermolecular hydrogen bonds the substituent effects are transmitted to the C=O group predominantly via the C=N-C=C part of the pyrimidinone ring. In the free molecules the transmission of substituent effects takes place mainly through the NH group.

AB - The C=O stretching frequencies of 32 5,6-polymethylenepyrimidin-4(3H)-one (1a-1w) and cis-5,6-polymethylene-5,6-dihydropyrimidin-4(3 H)-one (2a-2h) derivatives were measured in tetrachlormethane and in chloroform and correlated with the substituent constants X+ (R) in the sense of the modified and extended Seth-Paul-Van Duyse equation. It was found that the C=O stretching frequency and the transmission of substituent effects through the heterocyclic ring are significantly influenced by the size of the fused hydrocarbon ring. Evidence was obtained that in molecules linked by intermolecular hydrogen bonds the substituent effects are transmitted to the C=O group predominantly via the C=N-C=C part of the pyrimidinone ring. In the free molecules the transmission of substituent effects takes place mainly through the NH group.

KW - 5,6-Polymetylenepyrimidin-4(3H)-ones

KW - C=O Stretching frequencies

KW - Seth-Paul-Van Duyse equation

KW - Substituent effects

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