Evaluación de enlaces por puente de hidrógeno en hidrobenzotiazoles 2-piridin sustituidos

Jesús Alberto Alvarez-Hernández; Uvaldo Hernández-Balderas; Simplicio González-Montiel; José Guadalupe Alvarado-Rodríguez; Noemí Andrade-López

doi:10.29057/icbi.v3i6.570

Authors

Jesús Alberto Alvarez-Hernández Universidad Autónoma del Estado de Hidalgo
Uvaldo Hernández-Balderas Universidad Autónoma del Estado de Hidalgo
Simplicio González-Montiel Universidad Autónoma del Estado de Hidalgo
José Guadalupe Alvarado-Rodríguez Universidad Autónoma del Estado de Hidalgo
Noemí Andrade-López Universidad Autónoma del Estado de Hidalgo

DOI:

https://doi.org/10.29057/icbi.v3i6.570

Keywords:

Hydrogen bonds, 1H NMR, X-ray diffraction, hydrobenzothiazoles

Abstract

In this work, the study of hydrogen bonds in the hydrobenzothiazoles 2-pyridin substituted of general formula {(C6H4CSNH)(C5H4N)R} [(1), R = H; (2), R = C6H5; (3), R = C5H4N] in solution and solid state by NMR, infrared and X-ray diffraction is described, Figure 1. On the one hand, for 2 and 3, the 1H NMR data in CDCl3 solution displayed the predominance of an intramolecular hydrogen bonding NH•••N that is formed between the hydrogen atom of the NH group with the pyridinic nitrogen atom forming a five-membered ring. On the other hand, the 1H NMR spectra of 1 – 3 in DMSO-d6 solution showed the formation of intermolecular hydrogen bonds of type NH•••OS(CH3)2. In solid state, the NH•••N intramolecular hydrogen bonding for 1 – 3 by infrared and X-ray diffraction has been also established.

Downloads

Download data is not yet available.

Publication Facts

This article

Author statements

Data availability

N/A

16%

External funding

No

32%

Competing interests

N/A

11%

This journal

Other journals

Articles accepted

86%

33%

Days to publication

204

145

Indexed in

GS

Editor & editorial board: profiles
Academic society: N/A
Publisher: Universidad Autónoma del Estado de Hidalgo

References

Carlson, L., Welvy, J., Zebrowsky, K., Wilk, M., Giroux, R., Ciancio, N.,Tanskib, J. M., Bradley, A., Tyler, L.A. (2011) Spectroscopic differences between heterocyclic benzothiazoline, -thiazole and imine containing ligands and comparison of the Co and Cu pyridine benzothiazole and imine complexes. Inorganica Chimica Acta, 365(1), 159-166.

Dannenberg, J. (2005) The importance of cooperative interactions and a solid-state paradigm to proteins: what peptide chemists can learn from molecular crystals. Advances in Protein Chemistry, 72, 227-273.

Gaumont, A., Gulea, M., Levillain, J. (2009) Overview of the chemistry of 2-thiazolines. Chemical Reviews, 109(3), 1371-1401.

Gellman, S., Dado, G., Liang, G., Adams, B. (1991) Conformation-directing effects of a single intramolecular amide-amide hydrogen bond: variable-temperature NMR and IR studies on a homologous diamide series. Journal of the American Chemical Society, 113(4), 1164-1173.

Kuwabara, J., Mori, H., Kanbara, T. (2009) Crystal structure and intramolecular hydrogen bonding of a substituted diaminoquinoxaline. Heterocycles, 78(10), 2601-2607.

Lynna, M., Carlson, L., Hwangbo, H., Tanski, J., Tyler, L. (2012) Structural influences on the oxidation of a series of 2-benzothiazoline analogs. Journal of Molecular Structure, 1011, 81-93.

Yong-Hui, T., Kertesz, M. (2009) Low-bandgap pyrazine polymers: ladder-type connectivity by intramolecular S···N(sp2) interactions and hydrogen bonds. Macromolecules, 42(7), 2309-2312.

Yuan, L., Feng, W., Yamato, K., Sanford, A., Xu, D., Guo, H., Gong B. (2004) Highly efficient, one-step macrocyclizations assisted by the folding and preorganization of precursor oligomers. Journal of the American Chemical Society, 126(36), 11120-11121.

Zhan-Ting, L., Jun-Li, H. C. (2008) Peptide mimics by linear arylamides: A structural and functional diversity test. Accounts of Chemical Research, 41(10), 1343-1353.