Remarkably strong polarization of amidine fragment in the crystals of 1-imino-1H-isoindol-3-amine View Full Text


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Article Info

DATE

2013-08

AUTHORS

Oleg V. Shishkin, Irina S. Konovalova, Roman I. Zubatyuk, Gennady V. Palamarchuk, Svitlana V. Shishkina, Angelina V. Biitseva, Igor V. Rudenko, Volodymyr A. Tkachuk, Mikhail Yu. Kornilov, Olga V. Hordiyenko, Jerzy Leszczynski

ABSTRACT

Results of the X-ray diffraction studies of 1-imino-1H-isoindol-3-amine and its derivatives reveal unusual distribution of bond lengths within the NH2–C=N amidine fragment in the considered crystals. In the crystal phase, single C–N bond is shorter or at most has the same length as double C=N bond, while in isolated molecules both these bonds have expected lengths, according to the calculations by MP2/6-311G(d,p) and MP2/cc-pvtz methods. It is demonstrated that so unusually strong polarization of the amidine fragment is induced by polar environment in solid state. This effect stabilizes the amino-imino tautomer of 1-imino-1H-isoindol-3-amine, which becomes more stable than the diimino tautomer possessing the lowest energy in the gas phase. More... »

PAGES

1089-1097

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11224-012-0131-y

DOI

http://dx.doi.org/10.1007/s11224-012-0131-y

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1002033598


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33 schema:description Results of the X-ray diffraction studies of 1-imino-1H-isoindol-3-amine and its derivatives reveal unusual distribution of bond lengths within the NH2–C=N amidine fragment in the considered crystals. In the crystal phase, single C–N bond is shorter or at most has the same length as double C=N bond, while in isolated molecules both these bonds have expected lengths, according to the calculations by MP2/6-311G(d,p) and MP2/cc-pvtz methods. It is demonstrated that so unusually strong polarization of the amidine fragment is induced by polar environment in solid state. This effect stabilizes the amino-imino tautomer of 1-imino-1H-isoindol-3-amine, which becomes more stable than the diimino tautomer possessing the lowest energy in the gas phase.
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