The contribution of non-classical CHax⋯OC hydrogen bonds to the anomeric effect in fluoro and oxa-methoxycyclohexanes-Reference-Cited by-同舟云学术

The contribution of non-classical CHax⋯OC hydrogen bonds to the anomeric effect in fluoro and oxa-methoxycyclohexanes

Published:2021 Issue:10 Volume:23 Page:5845-5851
ISSN:1463-9076
Container-title:Physical Chemistry Chemical Physics
language:en
Short-container-title:Phys. Chem. Chem. Phys.

Author:

Piscelli Bruno A.¹²³⁴⁵,O’Hagan David⁶⁷⁸⁹¹⁰^ORCID,Cormanich Rodrigo A.¹²³⁴⁵^ORCID

Affiliation:

1. University of Campinas

2. Chemistry Institute

3. Monteiro Lobato Street

4. Campinas

5. Brazil

6. School of Chemistry

7. University of St Andrews

8. North Haugh

9. St Andrews

10. UK

Abstract

In this theory study the dominance of non-classical 1,3-diaxial CH_ax⋯OC hydrogen bonds (NCHBs) dictating anomeric effects in fluorinated methoxycyclohexanes and 2-methoxytetrahydropyrans is demonstrated, a phenomenon which is most often described as a consequence of hyperconjugation.

Funder

Engineering and Physical Sciences Research Council

Fundação de Amparo à Pesquisa do Estado de São Paulo

British Association for Psychopharmacology

Publisher

Royal Society of Chemistry (RSC)

Subject

Physical and Theoretical Chemistry,General Physics and Astronomy

Link

http://pubs.rsc.org/en/content/articlepdf/2021/CP/D0CP06646J

Reference29 articles.

1. Theoretical Evidence for the Relevance of n(F) → σ*(C–X) (X = H, C, O, S) Stereoelectronic Interactions