Stereoelectronic Properties of Tetrahedral Species derived from Carbonyl Groups. Ab initio study of the hydroxymethanes

Jean‐Marie Lehn; Georges Wipff; Hans‐Beat Bürgi

doi:10.1002/hlca.19740570225

Author(s)

Jean‐Marie Lehn
Georges Wipff
Hans‐Beat Bürgi

Detail(s)

Original language	English
Pages (from-to)	493-496
Journal / Publication	Helvetica Chimica Acta
Volume	57
Issue number	2
Publication status	Published - 1974
Externally published	Yes

Link(s)

DOI	DOI https://doi.org/10.1002/hlca.19740570225 Final Published version
	Check@CityULib
Link to Scopus	https://www.scopus.com/record/display.uri?eid=2-s2.0-84987263293&origin=recordpage
Permanent Link	https://scholars.cityu.edu.hk/en/publications/publication(50366fbc-d18a-47e5-8cee-4b7d81e09466).html

Abstract

Analysis of the electronic structure of the hydroxymethanes provides a consistent picture of stereoelectronic effects in such molecules: The average CO bond length decreases in the series methanol, methanediol, methanetriol. An oxygen (O′) lone pair, which is trans‐anti‐periplanar (app) to another oxygen (O″), shortens and strengthens the CO′ bond and simultaneously lengthens and weakens the CO′ bond. This is consistent with solid state structural evidence and with the reactivity patterns of tetrahedral species resulting from nucleophilic addition to a carbonyl group. Copyright © 1974 Verlag GmbH & Co. KGaA, Weinheim

Bibliographic Note

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Citation Format(s)

[ RIS ] [ BibTeX ]

Stereoelectronic Properties of Tetrahedral Species derived from Carbonyl Groups. Ab initio study of the hydroxymethanes. / Lehn, Jean‐Marie; Wipff, Georges; Bürgi, Hans‐Beat.
In: Helvetica Chimica Acta, Vol. 57, No. 2, 1974, p. 493-496.

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

Lehn, JM, Wipff, G & Bürgi, HB 1974, 'Stereoelectronic Properties of Tetrahedral Species derived from Carbonyl Groups. Ab initio study of the hydroxymethanes', Helvetica Chimica Acta, vol. 57, no. 2, pp. 493-496. https://doi.org/10.1002/hlca.19740570225

Lehn, JM., Wipff, G., & Bürgi, HB. (1974). Stereoelectronic Properties of Tetrahedral Species derived from Carbonyl Groups. Ab initio study of the hydroxymethanes. Helvetica Chimica Acta, 57(2), 493-496. https://doi.org/10.1002/hlca.19740570225

Lehn JM, Wipff G, Bürgi HB. Stereoelectronic Properties of Tetrahedral Species derived from Carbonyl Groups. Ab initio study of the hydroxymethanes. Helvetica Chimica Acta. 1974;57(2):493-496. doi: 10.1002/hlca.19740570225

Lehn, Jean‐Marie ; Wipff, Georges ; Bürgi, Hans‐Beat. / Stereoelectronic Properties of Tetrahedral Species derived from Carbonyl Groups. Ab initio study of the hydroxymethanes. In: Helvetica Chimica Acta. 1974 ; Vol. 57, No. 2. pp. 493-496.