The Gas Phase Protonation Sites of Six Naturally Occurring Nicotinoids

被引：1

作者：

Okura, Yuika ^{[1
]}

Santis, Garrett D. ^{[2
]}

Hirata, Keisuke ^{[1
,3
]}

Xantheas, Sotiris S. ^{[2
,3
,4
,5
]}

Fujii, Masaaki ^{[3
,6
,7
]}

Ishiuchi, Shun-Ichi ^{[1
,3
,6
]}

机构：

[1] Tokyo Inst Technol, Sch Sci, Dept Chem, Tokyo 152855, Japan

[2] Univ Washington, Dept Chem, Seattle, WA 98195 USA

[3] Tokyo Inst Technol, Inst Innovat Res, World Res Hub Initiat WRHI, Yokohama 2268503, Japan

[4] Pacific Northwest Natl Lab, Adv Comp Math & Data Div, Richland, WA 99352 USA

[5] Pacific Northwest Natl Lab, Computat & Theoret Chem Inst CTCI, Richland, WA 99352 USA

[6] Tokyo Inst Technol, Lab Chem & Life Sci, Inst Innovat Res, Yokohama 2268503, Japan

[7] Chuo Univ, Res & Dev Initiat, Tokyo 1128551, Japan

来源：

JOURNAL OF PHYSICAL CHEMISTRY LETTERS | 2024年

关键词：

BASIS-SETS; ION-TRAP; NORNICOTINE; SPECTROSCOPY; PHARMACOLOGY; ENERGY; COLD;

D O I：

10.1021/acs.jpclett.4c01206

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The gas phase protonation sites of six naturally occurring nicotinoids, namely nicotine (NIC), nornicotine (NOR), anabasine (ANB), anatabine (ANT), cotinine (COT), and myosmine (MYO), consisting of a common Pyridine and differing non-Pyridine rings, have been determined for the first time at the physiological temperature from cryogenic ion trap infrared spectroscopy and electronic structure calculations. The protonation site on either of these two rings is related to the nicotinoid's biological activity. At room temperature, NIC is a mixture of Pyridine and Pyrrolidine (non-Pyridine) protomers, whereas NOR, ANB, ANT, and COT are pure Pyridine protomers and finally MYO is mostly a Pyroline (non-Pyridine) protomer. The nearly planar structure of MYO-H+, induced by the presence of a conjugated pi system and confirmed from calculations and the UV absorption spectra, breaks from the trends observed for NIC, NOR, and ANB, since its structure is drastically different from the structures of the other nicotinoids.

引用

页码：6966 / 6973

页数：8

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