Deuterium isotope effects as evidence for substituent perturbation of the π‐electron frame in benzanilides

Martha S. Morales‐Ríos; Víctor Pérez‐Alvarez; Pedro Joseph‐Nathan; L. Gerardo Zepeda

doi:10.1002/mrc.1260320506

Deuterium isotope effects as evidence for substituent perturbation of the π‐electron frame in benzanilides

Martha S. Morales‐Ríos, Víctor Pérez‐Alvarez, Pedro Joseph‐Nathan, L. Gerardo Zepeda

Escuela Nacional de Ciencias Biológicas (ENCB)

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5 Scopus citations

Abstract

Deuterium isotope effects on ¹³C nuclear shielding, ⁿΔC(D), transmitted across a D‐labelled nitrogen atom were investigated for a series of para‐substituted benzanilides. The two two‐bond isotope shifts, ²ΔC(D) are perturbed essentially in a trough‐bond manner by change of the contribution of mesomeric structures. The magnitudes of ²Δ(CO) and ²Δ(C‐1′) are found to be mutually interdependent as evidenced by the linear relationships between the average values of ²Δ(CO) and ²Δ(C‐1′) with ¹H(NH) chemical shifts and with ¹⁵N SCS. This behaviour is interpreted as resulting from a cross‐conjugated transmission pathway involving the carbons sharing the D‐labelled nitrogen.

Original language	English
Pages (from-to)	288-291
Number of pages	4
Journal	Magnetic Resonance in Chemistry
Volume	32
Issue number	5
DOIs	https://doi.org/10.1002/mrc.1260320506
State	Published - Apr 1994

Keywords

Benzanilides
C NMR
Cross‐conjugated transmission
Deuterium isotope effects
NMR
Substituent effects

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10.1002/mrc.1260320506

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title = "Deuterium isotope effects as evidence for substituent perturbation of the π‐electron frame in benzanilides",

abstract = "Deuterium isotope effects on 13C nuclear shielding, nΔC(D), transmitted across a D‐labelled nitrogen atom were investigated for a series of para‐substituted benzanilides. The two two‐bond isotope shifts, 2ΔC(D) are perturbed essentially in a trough‐bond manner by change of the contribution of mesomeric structures. The magnitudes of 2Δ(CO) and 2Δ(C‐1′) are found to be mutually interdependent as evidenced by the linear relationships between the average values of 2Δ(CO) and 2Δ(C‐1′) with 1H(NH) chemical shifts and with 15N SCS. This behaviour is interpreted as resulting from a cross‐conjugated transmission pathway involving the carbons sharing the D‐labelled nitrogen.",

keywords = "Benzanilides, C NMR, Cross‐conjugated transmission, Deuterium isotope effects, NMR, Substituent effects",

author = "Morales‐R{\'i}os, {Martha S.} and V{\'i}ctor P{\'e}rez‐Alvarez and Pedro Joseph‐Nathan and Zepeda, {L. Gerardo}",

year = "1994",

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doi = "10.1002/mrc.1260320506",

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TY - JOUR

T1 - Deuterium isotope effects as evidence for substituent perturbation of the π‐electron frame in benzanilides

AU - Morales‐Ríos, Martha S.

AU - Pérez‐Alvarez, Víctor

AU - Joseph‐Nathan, Pedro

AU - Zepeda, L. Gerardo

PY - 1994/4

Y1 - 1994/4

N2 - Deuterium isotope effects on 13C nuclear shielding, nΔC(D), transmitted across a D‐labelled nitrogen atom were investigated for a series of para‐substituted benzanilides. The two two‐bond isotope shifts, 2ΔC(D) are perturbed essentially in a trough‐bond manner by change of the contribution of mesomeric structures. The magnitudes of 2Δ(CO) and 2Δ(C‐1′) are found to be mutually interdependent as evidenced by the linear relationships between the average values of 2Δ(CO) and 2Δ(C‐1′) with 1H(NH) chemical shifts and with 15N SCS. This behaviour is interpreted as resulting from a cross‐conjugated transmission pathway involving the carbons sharing the D‐labelled nitrogen.

AB - Deuterium isotope effects on 13C nuclear shielding, nΔC(D), transmitted across a D‐labelled nitrogen atom were investigated for a series of para‐substituted benzanilides. The two two‐bond isotope shifts, 2ΔC(D) are perturbed essentially in a trough‐bond manner by change of the contribution of mesomeric structures. The magnitudes of 2Δ(CO) and 2Δ(C‐1′) are found to be mutually interdependent as evidenced by the linear relationships between the average values of 2Δ(CO) and 2Δ(C‐1′) with 1H(NH) chemical shifts and with 15N SCS. This behaviour is interpreted as resulting from a cross‐conjugated transmission pathway involving the carbons sharing the D‐labelled nitrogen.

KW - Benzanilides

KW - C NMR

KW - Cross‐conjugated transmission

KW - Deuterium isotope effects

KW - NMR

KW - Substituent effects

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U2 - 10.1002/mrc.1260320506

DO - 10.1002/mrc.1260320506

M3 - Artículo

SN - 0749-1581

VL - 32

SP - 288

EP - 291

JO - Magnetic Resonance in Chemistry

JF - Magnetic Resonance in Chemistry

IS - 5

ER -

Deuterium isotope effects as evidence for substituent perturbation of the π‐electron frame in benzanilides

Abstract

Keywords

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