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

Research output: Contribution to journalArticleResearchpeer-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 languageEnglish
Pages (from-to)3372-3376
JournalJ. Org. Chem.
Volume56
Issue number10
DOIs
Publication statusPublished - 1 May 1991

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