13C NMR Chemical Shifts. A Single Rule To Determine the Conformation of Calix[4]arenes

Carlos Jaime; Javier de Mendoza; Pilar Prados; Pedro M. Nieto; Concha Sánchez

doi:10.1021/jo00010a036

¹³C NMR Chemical Shifts. A Single Rule To Determine the Conformation of Calix[4]arenes

Carlos Jaime, Javier de Mendoza, Pilar Prados, Pedro M. Nieto, Concha Sánchez

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

585 Citations (Scopus)

Abstract

The conformations of calix[4]arenes can be deduced from the 13C NMR chemical shift of the methylene groups connecting each pair of aromatic rings. Inspection of 24 cases revealed that when the phenol rings beside each methylene are in a syn orientation (i.e., in cone conformations), the methylene signals appear around δ 31, whereas they appear around δ 37 when both phenol rings are anti oriented (i.e., in 1, 3-alternate conformations). Steric effects are believed to be the main cause of such large differences. © 1991, American Chemical Society. All rights reserved.

Original language	English
Pages (from-to)	3372-3376
Journal	J. Org. Chem.
Volume	56
Issue number	10
DOIs	https://doi.org/10.1021/jo00010a036
Publication status	Published - 1 May 1991

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title = "13C NMR Chemical Shifts. A Single Rule To Determine the Conformation of Calix[4]arenes",

abstract = "The conformations of calix[4]arenes can be deduced from the 13C NMR chemical shift of the methylene groups connecting each pair of aromatic rings. Inspection of 24 cases revealed that when the phenol rings beside each methylene are in a syn orientation (i.e., in cone conformations), the methylene signals appear around δ 31, whereas they appear around δ 37 when both phenol rings are anti oriented (i.e., in 1, 3-alternate conformations). Steric effects are believed to be the main cause of such large differences. {\textcopyright} 1991, American Chemical Society. All rights reserved.",

author = "Carlos Jaime and {de Mendoza}, Javier and Pilar Prados and Nieto, {Pedro M.} and Concha S{\'a}nchez",

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doi = "10.1021/jo00010a036",

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AU - Jaime, Carlos

AU - de Mendoza, Javier

AU - Prados, Pilar

AU - Nieto, Pedro M.

AU - Sánchez, Concha

PY - 1991/5/1

Y1 - 1991/5/1

N2 - The conformations of calix[4]arenes can be deduced from the 13C NMR chemical shift of the methylene groups connecting each pair of aromatic rings. Inspection of 24 cases revealed that when the phenol rings beside each methylene are in a syn orientation (i.e., in cone conformations), the methylene signals appear around δ 31, whereas they appear around δ 37 when both phenol rings are anti oriented (i.e., in 1, 3-alternate conformations). Steric effects are believed to be the main cause of such large differences. © 1991, American Chemical Society. All rights reserved.

AB - The conformations of calix[4]arenes can be deduced from the 13C NMR chemical shift of the methylene groups connecting each pair of aromatic rings. Inspection of 24 cases revealed that when the phenol rings beside each methylene are in a syn orientation (i.e., in cone conformations), the methylene signals appear around δ 31, whereas they appear around δ 37 when both phenol rings are anti oriented (i.e., in 1, 3-alternate conformations). Steric effects are believed to be the main cause of such large differences. © 1991, American Chemical Society. All rights reserved.

U2 - 10.1021/jo00010a036

DO - 10.1021/jo00010a036

M3 - Article

VL - 56

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