Issue 1, 2011
From the journal:

CrystEngComm

Covalent assistance to supramolecular synthesis: directing the supramolecular assembly of co-crystals by in situ modification of hydrogen bonding functionality†

Andreas Lemmerer,*a   Joel Bernstein*b  and  Volker Kahlenbergc  

* Corresponding authors

a Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Johannesburg, South Africa
E-mail: andreas.lemmerer@gmail.com
Fax: +27 11 717 6749
Tel: +27 11 717 6723

b Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva, Israel
E-mail: yoel@bgu.ac.il
Fax: +972 8 647 2943
Tel: +972 8 647 2455

c Institute of Mineralogy and Petrography, University of Innsbruck, Innsbruck, Austria
Fax: +43 512 507 2926
Tel: +43 512 507 5503

Abstract

Nicotinic acid hydrazide (niazid) readily co-crystallizes with carboxylic acids in methanol to form a 2-D sheet structure that utilizes all three H bond donors on the carbohydrazide functional group. In acetone solution niazid undergoes a condensation reaction with the solvent, which replaces the amine group with a hydrocarbon group leaving only one hydrogen bond donor on the modified niazid molecule, now containing a N-acylhydrazone functional group. The resulting reduced hydrogen bonding functionality leads to a new supramolecular assembly when co-crystallized with the same dicarboxylic acids.

Graphical abstract: Covalent assistance to supramolecular synthesis: directing the supramolecular assembly of co-crystals by in situ modification of hydrogen bonding functionality

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Article information

DOI
https://doi.org/10.1039/C0CE00347F
Article type
Communication
Submitted
28 Jun 2010
Accepted
05 Oct 2010
First published
01 Nov 2010

CrystEngComm, 2011,13, 55-59

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Covalent assistance to supramolecular synthesis: directing the supramolecular assembly of co-crystals by in situ modification of hydrogen bonding functionality

A. Lemmerer, J. Bernstein and V. Kahlenberg, CrystEngComm, 2011, 13, 55 DOI: 10.1039/C0CE00347F

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