The unsubstituted ortho-amidino benzoic acid : crystal structure, characterization and pKa determination

Hordiyenko, Olga V.; Biitseva, Angelina V.; Kostina, Yuliya Yu.; Zubatyuk, Roman I.; Shishkin, Oleg V.; Groth, Ulrich; Kornilov, Mikhail Yu.

The unsubstituted ortho-amidino benzoic acid : crystal structure, characterization and pKa determination

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Date

2017

Authors

Hordiyenko, Olga V.

Biitseva, Angelina V.

Kostina, Yuliya Yu.

Zubatyuk, Roman I.

Shishkin, Oleg V.

Groth, Ulrich

Kornilov, Mikhail Yu.

DOI (citable link)

10.1007/s11224-016-0822-x

Collections

Chemie

Publication type

Journal article

Publication status

Published

Published in

Structural Chemistry ; 28 (2017), 3. - pp. 607-616. - ISSN 1040-0400. - eISSN 1572-9001

Abstract

The simplest o-amidino benzoic acid—2-(amino(imino)methyl)benzoic acid—has been isolated in 23 % yield as a side product of the reaction of phthalonitrile and ammonia along with desired 1-imino-1H-isoindol-3-amine. This amidino acid was fully characterized by nuclear magnetic resonance, IR spectroscopy, mass spectrometry; pKa values were also determined. X-ray diffraction study and quantum chemical calculations revealed that in the solid state it exists as a zwitterion that is stabilized by intermolecular hydrogen bonds.

Subject (DDC)

540 Chemistry

Cite This

ISO 690

HORDIYENKO, Olga V., Angelina V. BIITSEVA, Yuliya Yu. KOSTINA, Roman I. ZUBATYUK, Oleg V. SHISHKIN, Ulrich GROTH, Mikhail Yu. KORNILOV, 2017. The unsubstituted ortho-amidino benzoic acid : crystal structure, characterization and pKa determination. In: Structural Chemistry. 28(3), pp. 607-616. ISSN 1040-0400. eISSN 1572-9001. Available under: doi: 10.1007/s11224-016-0822-x

BibTex

@article{Hordiyenko2017unsub-39224,
  year={2017},
  doi={10.1007/s11224-016-0822-x},
  title={The unsubstituted ortho-amidino benzoic acid : crystal structure, characterization and pKa determination},
  number={3},
  volume={28},
  issn={1040-0400},
  journal={Structural Chemistry},
  pages={607--616},
  author={Hordiyenko, Olga V. and Biitseva, Angelina V. and Kostina, Yuliya Yu. and Zubatyuk, Roman I. and Shishkin, Oleg V. and Groth, Ulrich and Kornilov, Mikhail Yu.}
}

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