Molecular Structure of 2,3-Dicyano-5,7,7-trimethyl-6,7-dihydro-1H-1,4-diazepine - Precursor of pH-Sensitive Porphyrazines

Ivan A. Skvortsov,^a Alina M. Fazlyeva,^a Nikolay V. Somov,^b and Pavel A. Stuzhin^a@

^aResearch Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology (ISUCT), 153000 Ivanovo, Russian Federation

^bLobachevsky State University, 603950 Nizhnij Novgorod, Russian Federation

^@Corresponding author E-mail: stuzhin@isuct.ru

Dedicated to Professor Olga G. Khelevina on the occasion of her Anniversary

DOI 10.6060/mhc210750s
Macroheterocycles 2021 14(3) 198-200

Molecular structure of 2,3-dicyano-5,7,7-trimethyl-6,7-dihydro-1H-1,4-diazepine, which was recently used as precursor for pH-sensitive porphyrazine fluorophores (New J. Chem. 2020, DOI: 10.1039/d0nj04388e), was determined by single crystal X-ray diffraction analysis. The obtained structural data confirm the conclusions made on the basis ofspectral study and quantum-chemical modelling and evidence that –N= and –NH– groups in 6,7-dihydro-1H-1,4-diazepine ring can be considered as pyridine- and pyrrole-type nitrogens, and the electronic lone pair of the latter is involved in formation of quasi-aromatic conjugated heterocyclic system.

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Molecular Structure of 2,3-Dicyano-5,7,7-trimethyl-6,7-dihydro-1H-1,4-diazepine - Precursor of pH-Sensitive Porphyrazines

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