A “V”-shaped Hammett plot shows that resonance-assisted hydrogen bonding does not dictate the strength of the intramolecular hydrogen bond in the E isomers of hydrazone-based switches because it involves an aromatic pyridyl ring.
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Unusual para-substituent effects on the intramolecular hydrogen-bond in hydrazone-based switches
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a
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA
E-mail: ivan.aprahamian@dartmouth.edu
E-mail: ivan.aprahamian@dartmouth.edu
b
Institute of Chemistry, University of Tartu, Ravila 14a, 50411 Tartu, Estonia
E-mail: ivo.leito@ut.ee
E-mail: ivo.leito@ut.ee
Chem. Commun., 2012,48, 10490-10492
DOI: 10.1039/C2CC35860C
Received 27 Jun 2012, Accepted 31 Aug 2012
First published online 04 Sep 2012
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Aromaticity
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