Issue 23, 2011
From the journal:

CrystEngComm

The use of the triptycene framework for observing O⋯C[double bond, length as m-dash]O molecular interactions†

Alberth Lari,a   Mateusz B. Pitak,b   Simon J. Coles,b   Emma Bresco,a   Peter Belser,c   Andreas Beyeler,c   Melanie Pilkingtond  and  John D. Wallis*a  

* Corresponding authors

a School of Science and Technology, Nottingham Trent University, Clifton Lane, Nottingham, UK
E-mail: john.wallis@ntu.ac.uk

b National Crystallography Service, School of Chemistry, University of Southampton, Highfield Campus, Southampton, UK

c Department of Chemistry, University of Fribourg, Chemin du Musée 9, Fribourg, Switzerland

d Department of Chemistry, Brock University, 500 Glenridge Ave, St Catharines, Ontario, Canada

Abstract

The triptycene skeleton has been used to measure (1,5) interactions between aldehyde groups, placed at both sp3 centres, and hydroxy or methoxy groups, placed at the respective ortho position on a benzene ring; HO⋯CHO interactions of 2.621–2.624 Å and MeO⋯CHO interactions of 2.528–2.584 Å were observed with the O⋯C vector making angles of 105.3–133.7° with the carbonyl bond. The lack of a competing conjugation with the framework for the electrophilic group is a favourable factor compared to the use of peri-naphthalene systems.

Graphical abstract: The use of the triptycene framework for observing O⋯C [[double bond, length as m-dash]] O molecular interactions

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Article information

DOI
https://doi.org/10.1039/C1CE05955F
Article type
Paper
Submitted
27 Jul 2011
Accepted
13 Sep 2011
First published
04 Oct 2011

CrystEngComm, 2011,13, 6978-6984

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The use of the triptycene framework for observing O⋯C[double bond, length as m-dash]O molecular interactions

A. Lari, M. B. Pitak, S. J. Coles, E. Bresco, P. Belser, A. Beyeler, M. Pilkington and J. D. Wallis, CrystEngComm, 2011, 13, 6978 DOI: 10.1039/C1CE05955F

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