Issue 6, 2016

Two modes of peri-interaction between an aldehyde group and a carboxylate anion in naphthalaldehydate salts

Abstract

Crystal structures of the salts of 1,8-naphthalaldehydic acid (8-formyl-1-naphthoic acid) show one of two types of interaction between the functional groups. In the more commonly observed case, a carboxylate oxygen lies close to the aldehyde carbonyl carbon atom (O⋯C: 2.445–2.630 Å) and makes an n–pi* interaction. However, in two other cases the carboxylate group has rotated so that the aldehyde now directs its hydrogen atom at the face of the carboxylate group and forms a surprisingly short contact with the carbon atom (H⋯C: 2.29 and 2.42 Å). This interaction is likely to be electrostatic in nature.

Graphical abstract: Two modes of peri-interaction between an aldehyde group and a carboxylate anion in naphthalaldehydate salts

Supplementary files

Article information

Article type
Paper
Submitted
23 Nov 2015
Accepted
31 Dec 2015
First published
04 Jan 2016
This article is Open Access
Creative Commons BY license

CrystEngComm, 2016,18, 948-961

Author version available

Two modes of peri-interaction between an aldehyde group and a carboxylate anion in naphthalaldehydate salts

G. Saritemur, L. Nomen Miralles, D. Husson, M. B. Pitak, S. J. Coles and J. D. Wallis, CrystEngComm, 2016, 18, 948 DOI: 10.1039/C5CE02282G

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