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The Studies of Structure of 2N‐(3‐phenyl‐allyl‐)(5‐phenyl‐[1,3,4] Thiadiazol‐2‐yl) Amine in Solution
Author(s) -
Strzemecka Leokadia,
Fijałkowski Łukasz,
Nowaczyk Alicja
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2683
Subject(s) - tautomer , chemistry , amine gas treating , imine , ionic bonding , spectroscopy , nuclear magnetic resonance spectroscopy , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , carbon 13 nmr , resonance (particle physics) , medicinal chemistry , crystallography , computational chemistry , organic chemistry , ion , catalysis , physics , particle physics , quantum mechanics
2N‐(3‐phenyl‐allyl‐)(5‐phenyl‐[1,3,4] thiadiazol‐2‐yl) amine was studied by means of the 1 H, 13 C, 15 N NMR spectroscopy and DFT calculations. On the basis of the one‐dimensional 1 H, 13 C, 15 N‐NMR and two‐dimensional 1 H‐ 13 C HMQC, 1 H‐ 13 C HMBC, 1 H‐ 15 N HMQC, 1 H 1 H NOESY, 1 H 1 H COSY correlation spectra the amine‐type and the imine‐type tautomers have been determined in the solution. Variety of structural forms including: biradical, ionic–biradical, and ionic structures of the amine‐type a and of the imine‐type b , c tautomers exist in the solution. According to the DFT computations the differences in the total energy between a and b , a and c , and b and c tautomers are equal to 1.5 kJ/mol, 1.2 kJ/mol, and 0.3 kJ/mol, respectively.