吡唑和茚唑的n -杂环烯烃

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-28 DOI:10.1021/acs.orglett.5c0077510.1021/acs.orglett.5c00775

Bolin Zhu, Rouven Woyciechowski, Eike G. Hübner, Felix Lederle and Andreas Schmidt*,

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引用次数: 0

摘要

3-甲基吡唑和3-甲基林唑盐类的脱质子反应产率很高，可与异氰酸酯、卤素和二硫化碳反应生成n -杂环烯烃（NHOs）。计算出的质子亲和力分别为261千卡/mol（茚唑NHOs）和272千卡/mol（吡唑NHOs）。计算的pKa值在14.8 ~ 25.2之间，外环双键的键长略短于咪唑NHOs的键长。正如预期的那样，最高占据的分子轨道在外环碳原子上显示出显著的原子轨道系数。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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N-Heterocyclic Olefins of Pyrazole and Indazole

Deprotonation of 3-methylpyrazolium and 3-methylindazolium salts yielded N-heterocyclic olefins (NHOs) in excellent yields, which reacted with isocyanates, halogens, and carbon disulfide. Calculated proton affinities are 261 kcal/mol (indazole NHOs) and 272 kcal/mol (pyrazole NHOs). The calculated pK_a values are between 14.8 and 25.2, and bond lengths of the exocyclic double bond are slightly shorter than those of imidazole NHOs. As expected, the highest occupied molecular orbitals show significant atomic orbital coefficients at the exocyclic carbon atom.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.