On the acidity of cyclopropanaphthalenes - Gas phase and computational studies

被引：7

作者：

Antol, I

Glasovac, Z

Hare, MC

Eckert-Maksic, M

Kass, SR

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

[2] Rudjer Boskovic Inst, Div Organ Chem & Biochem, HR-10002 Zagreb, Croatia

来源：

INTERNATIONAL JOURNAL OF MASS SPECTROMETRY | 2003年 / 222卷 / 1-3期

基金：

美国国家科学基金会;

关键词：

aromaticity; antiaromaticity; cycloproparenes; FTMS; ab initio; DFT calculations;

D O I：

10.1016/S1387-3806(02)00953-3

中图分类号：

O64 [物理化学（理论化学）、化学物理学]; O56 [分子物理学、原子物理学];

学科分类号：

070203 ; 070304 ; 081704 ; 1406 ;

摘要：

1H-Cyclopropa[b] naphthalene (3H) and 2-methylnaphthalene (6H) were deprotonated by fluoride ion in a Fourier transform mass spectrometer, and their acidities were measured via equilibrium techniques (DeltaGdegrees(acid) = 357.5 +/- 2.1 kcal mol(-1) (3H) and 365.2 +/- 2.1 kcal mol(-1) (6H), DeltaH(acid)degrees = 365.1 +/- 2.1 kcal mol(-1) (3H) and 372.7 +/- 2.1 kcal mol(-1) (6H)). These results were modeled by MP2 and BVWN5 calculations, and additional computations were carried out on benzocyclopropene (1H), toluene (2H), IH-cyclopropa[a]naphthalene (4H), and 1-methylnaphthalene (5H). The stability of the conjugate bases of 3H and 4H are examined and their aromatic vs. antiaromatic nature is considered.

引用

页码：11 / 26

页数：16

共 72 条

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[Anonymous], 1979, COULSONS VALENCE

[2] Formation of transient and long-lived cyclopropenyl anions [J].