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Publication
Structural investigation of nitrogen-linked saccharinate–tetrazole
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Advisor(s)
Abstract(s)
The molecular structure of nitrogen-linked saccharinate–tetrazole, N-(1,1-dioxo-1,2-benzisothiazol-3-yl)-amine-1H-tetrazole (BAT), was investigated in the crystalline state using X-ray crystallography and
infrared and Raman spectroscopies, and isolated in argon matrix by infrared spectroscopy. Interpretation of the experimental results was supported by quantum chemical calculations undertaken at the DFT(B3LYP)/6-311++G(3df,3pd) level of theory. In the neat crystalline solid (space group C2/c, a = 21.7493(3) Å, b = 8.85940(10) Å, c = 10.76900(10) Å, b = 103.3300(10) deg; Z = 8), BAT units exist in the (1H)-tetrazole aminosaccharin tautomeric form, with the NH spacer establishing a hydrogen bond to the nitrogen in position-4 of the tetrazole group of a neighbour molecule, and the NH group of the tetrazole fragment forming a bifurcated H-bond to the saccharyl nitrogen of the same molecule and to one of the oxygen atoms of a second neighbour molecule. On the other hand, according to both the matrix isolation infrared studies and the theoretical calculations, the isolated BAT molecule exists preferentially
as the (1H)-tetrazole iminosaccharin tautomer, where the main stabilizing interaction is the intramolecular H-bond established between the NH group of the saccharyl ring and the tetrazole nitrogen atom in position 4. A detailed conformational analysis of the studied molecule and full assignment of the vibrational spectra for both the matrix-isolated compound and crystalline sample were undertaken.
Description
Keywords
Saccharinate-tetrazole Conformational analysis X-ray crystallography DFT calculations Matrix-isolation infrared spectroscopy Solid state infrared and Raman Spectroscopies
Citation
Gómez-Zavaglia, A.; Ismael, A.; Cabral, L.I.L.; Kaczor, A.; Paixão, J.A.; Fausto, R.; Cristiano, M.L.S. Structural investigation of nitrogen-linked saccharinate–tetrazole, Journal of Molecular Structure, 1003, 1-3, 103-110, 2011.
Publisher
Elsevier