Crystalstructure analysis of 5,6-dimethylimidazo[2,1-b ]-1,3,4-thiadiazole (3) and its corresponding hydrobromide has shown that protonation occurs at N(7). Molecular properties, mainly aromaticity and basicity, of this system were interpreted on the basis of semi-empirically calculated ring-current, whic show that this molecules has a lower aromatic character than that of other fused heterocycles of imidazole with pyrimidine and thiazole rings. From 1-H nmr measurements the protonation site in acidic solution coul not be determined, but N(7) was found to be the site available for complex formation in the presence of a lanthanide shut reagent.

Structure and Protonation Study of the Imidazo[2.1-b]-1,3,4-thiadiazole System: 1H Nuclear Magnetic Resonance, Crystal and Molecular Structure of 5,6-Dimethylimidazo[2,1-b]-1,3,4-thiadiazole and its Hydrobrimide / Schenetti, Luisa; Taddei, Ferdinando; L., Greci; L., Marchetti; G., Milani; G., Andreetti; G., Bocelli; P., Sgarabotto. - In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS II. - ISSN 0300-9580. - STAMPA. - na:(1980), pp. 412-421.

Structure and Protonation Study of the Imidazo[2.1-b]-1,3,4-thiadiazole System: 1H Nuclear Magnetic Resonance, Crystal and Molecular Structure of 5,6-Dimethylimidazo[2,1-b]-1,3,4-thiadiazole and its Hydrobrimide

SCHENETTI, Luisa;TADDEI, Ferdinando;
1980

Abstract

Crystalstructure analysis of 5,6-dimethylimidazo[2,1-b ]-1,3,4-thiadiazole (3) and its corresponding hydrobromide has shown that protonation occurs at N(7). Molecular properties, mainly aromaticity and basicity, of this system were interpreted on the basis of semi-empirically calculated ring-current, whic show that this molecules has a lower aromatic character than that of other fused heterocycles of imidazole with pyrimidine and thiazole rings. From 1-H nmr measurements the protonation site in acidic solution coul not be determined, but N(7) was found to be the site available for complex formation in the presence of a lanthanide shut reagent.
na
412
421
Structure and Protonation Study of the Imidazo[2.1-b]-1,3,4-thiadiazole System: 1H Nuclear Magnetic Resonance, Crystal and Molecular Structure of 5,6-Dimethylimidazo[2,1-b]-1,3,4-thiadiazole and its Hydrobrimide / Schenetti, Luisa; Taddei, Ferdinando; L., Greci; L., Marchetti; G., Milani; G., Andreetti; G., Bocelli; P., Sgarabotto. - In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS II. - ISSN 0300-9580. - STAMPA. - na:(1980), pp. 412-421.
Schenetti, Luisa; Taddei, Ferdinando; L., Greci; L., Marchetti; G., Milani; G., Andreetti; G., Bocelli; P., Sgarabotto
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11380/744495
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