Terahertz Spectroscopic and Density Functional Theoretical Analysis of Cocrystal Between Olmesartan and Benzoic Acid†

doi:10.7503/cjcu20150351

Abstract

Abstract:

The structure of cocrystal between olmesartan and benzoic acid was deterimined via terahertz time-domain spectroscopy(THz-TDS) technique and density functional theory(DFT). Experimental results show that all of them have distinctive and different fingerprint spectra in the THz region. The absorption peaks of olmesartan were at 0.53, 0.98, 1.09 THz and the absorption peaks of benzoic acid were at 0.65, 0.89, 1.10 THz. Characteristic bands observing in the terahertz spectra of cocrystal were at 0.64 and 1.33 THz, which were greatly different from corresponding raw starting materials. According to the structural characteristic of olmesartan molecule, density functional theory(DFT) program was used to simulate molecular structures and corresponding frequencies of olmesartan and three possible cocrystal forms considering the position of hydrogen bond formation between olmesartan and benzoic acid. The theoretical result showed that simulated olmesartan molecule had absorption peaks at 0.76, 1.05 and 1.27 THz, which was agreement with the THz experimental result. In addition, the theoretical results of three possible simulated cocrystal structures showed that FormⅠof simulated cocrystal was much better agreement with the experimental result than others. Therefore, the structure of cocrystal was confirmed that the first hydrogen bond was formed between amino group of olmesartan and hydroxyl group of benzoic acid, while the second one was formed between nitrogen atom of five nitrogen ring in olmesartan and carbonyl group of benzoic acid. The characteristic absorption bands of cocrystal between olmesartan and benzoic acid were also assigned based on the simulation results of DFT calculation.

Key words: Olmesartan, Benzoic acid, Cocrystal, Terahertz time-domain spectroscopy(THz-TDS), Density functional theory

CLC Number:

O641
O657.3

TrendMD:

FANG Hongxia, ZHANG Qi, ZHANG Huili, QIN Dan, HONG Zhi, DU Yong. Terahertz Spectroscopic and Density Functional Theoretical Analysis of Cocrystal Between Olmesartan and Benzoic Acid^†[J]. Chem. J. Chinese Universities, 2015, 36(12): 2504.

Figures/Tables 10

Fig.1 Molecular structure of olmesartan

Fig.2 Three theoretical structures of cocrystal between olmesartan and benzoic acid (1) FormⅠ; (B) form Ⅱ; (C) form Ⅲ.

Fig.3 Comparison of experimental(a) and theoretical(b) THz absorption spectra of olmesartan

Table 1 Comparison and assignment of theoretical spectrum and experimental spectrum for olmesartan

Frequency/THz		Vibrational mode
Expt.		Theo.
0.53	0.76	R3, N16H of R1 bending out of plane
0.98	1.05	C42—C45—C48, O11H, C8—C39—C52 and R1 bending out of plane
1.09	1.27	C42—C45—C48 and C39—C8—C5—C9 scissoring

Fig.4 Vibrational modes of olmesartan at 0.53 THz(A), 0.98 THz(B) and 1.09 THz(C)

Fig.5 THz spectra of olmesartan, benzoic acid and their cocrystal a. Cocrystal; b. olmesartan; c. physical mixture; d. benzoic acid.

Fig.6 Comparison of experimental(a) and theoretical forms Ⅰ(b), Ⅱ(c), Ⅲ(d) THz absorption spectra of cocrystal between olmesartan and benzoic acid

Table 2 Change of bond length of cocrystal between olmesartan and benzoic acid

Chemical bond	Bond length/nm
Chemical bond	Olmesartan	Benzoic acid	Cocrystal
C71=O72	—	0.1215	0.1231
C71—O73	—	0.1358	0.1329
O73—H74	—	0.9714	0.9965
N16—H38	0.1010	—	0.1028
N15—N16	0.1350	—	0.1343

Table 3 Vibration modes assginment of cocrystal between olmesartan and benzoic acid

Absorption peak frequency/THz	Vibrational mode
0.69	Benzoic acid and R1 twisting; R1, R2, C6—C42—C45—C48, C5—C9OOH and C56—C39—C52 bending out of plane
1.03	—C71OOH and R1 bending out of plane; the phenyl ring of benzoic acid and R2 bending out of plane; C6—C42—C45—C48, C5—C9OOH and C56—C3—C52 scissoring
1.58	R3 bending out of plane

Fig.7 Vibrational modes of theoretical cocrystal form Ⅰ between olmesartan and benzoic acid at 0.69 THz(A), 1.03 THz(B) and 1.58 THz(C)

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