N-H···O hydrogen bonding to the alkoxy oxygen of a carboxylic ester group: crystal structures of methyl 2,6-diaminobenzoate and its derivatives

Wallis, J.D. ORCID: 0000-0001-7259-8783, Garner, A.C. ORCID: 0000-0003-2488-0623 and Yang, S., 2020. N-H···O hydrogen bonding to the alkoxy oxygen of a carboxylic ester group: crystal structures of methyl 2,6-diaminobenzoate and its derivatives. CrystEngComm. ISSN 1466-8033

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Abstract

Methyl 2,6-diaminobenzoate and its bis-triphenylboron complex show hydrogen bonding from NH2 groups to both oxygen atoms of the carboxylic ester, and there is little difference in the lengths of these types of hydrogen bond, while the crystal structure of the tetrafluoroborate salt is dominated by cation/anion hydrogen bonding. In the mono N-tosyl derivative, the tosyl-N-H group forms a hydrogen bond to the carbonyl and the primary amino group makes a hydrogen bond to the alkoxy group, despite only the primary amino group the donating electron density into the ester group. A search of the Cambridge Structural Database reveals a number of examples of N-H···O hydrogen bonding to the alkoxy oxygen of an ester group with a preference for the N-H bond lying in the ester plane. Hydrogen bonding to the ester alkoxy group should not be excluded when considering mechanistic processes in chemical or biochemical systems.

Item Type: Journal article
Publication Title: CrystEngComm
Creators: Wallis, J.D., Garner, A.C. and Yang, S.
Publisher: Royal Society of Chemistry
Date: 6 May 2020
ISSN: 1466-8033
Identifiers:
NumberType
10.1039/d0ce00495bDOI
1323691Other
Divisions: Schools > School of Science and Technology
Depositing User: Linda Sullivan
Date Added: 07 May 2020 07:54
Last Modified: 07 May 2020 07:54
URI: http://irep.ntu.ac.uk/id/eprint/39796

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