On the acidity of cyclopropanaphthalenes: Gas phase and computational studies

Ivana Antol; Zoran Glasovac; Michael C. Hare; Mirjana Eckert-Maksic; Steven R. Kass

doi:10.1016/S1387-3806(02)00953-3

On the acidity of cyclopropanaphthalenes: Gas phase and computational studies

Ivana Antol, Zoran Glasovac, Michael C. Hare, Mirjana Eckert-Maksic, Steven R. Kass

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

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 (ΔG°_acid=357.5±2.1kcal mol^-1 (3H) and 365.2±2.1kcal mol^-1 (6H), ΔH°_acid=365.1±2.1kcal mol^-1 (3H) and 372.7±2.1kcal mol^-1 (6H)). These results were modeled by MP2 and BVWN5 calculations, and additional computations were carried out on benzocyclopropene (1H), toluene (2H), 1H-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.

Original language	English (US)
Pages (from-to)	11-26
Number of pages	16
Journal	International Journal of Mass Spectrometry
Volume	222
Issue number	1-3
DOIs	https://doi.org/10.1016/S1387-3806(02)00953-3
State	Published - Jan 1 2003

Bibliographical note

Funding Information:
Support from the National Science Foundation, the donors of the Petroleum Research Foundation, as administered by the American Chemical Society, the Minnesota Supercomputer Institute, and the University of Minnesota-IBM Shared Research Project are gratefully acknowledged. The work in Zagreb (I.A., Z.G., and M.E.M.) has been supported by the Ministry of Science and Technology of Croatia through project 00980801 and HR-US project JF 143.

Keywords

Ab initio
Antiaromaticity
Aromaticity
Cycloproparenes
DFT calculations
FTMS

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10.1016/S1387-3806(02)00953-3

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title = "On the acidity of cyclopropanaphthalenes: Gas phase and computational studies",

abstract = "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 (ΔG°acid=357.5±2.1kcal mol-1 (3H) and 365.2±2.1kcal mol-1 (6H), ΔH°acid=365.1±2.1kcal mol-1 (3H) and 372.7±2.1kcal mol-1 (6H)). These results were modeled by MP2 and BVWN5 calculations, and additional computations were carried out on benzocyclopropene (1H), toluene (2H), 1H-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.",

keywords = "Ab initio, Antiaromaticity, Aromaticity, Cycloproparenes, DFT calculations, FTMS",

author = "Ivana Antol and Zoran Glasovac and Hare, {Michael C.} and Mirjana Eckert-Maksic and Kass, {Steven R.}",

note = "Funding Information: Support from the National Science Foundation, the donors of the Petroleum Research Foundation, as administered by the American Chemical Society, the Minnesota Supercomputer Institute, and the University of Minnesota-IBM Shared Research Project are gratefully acknowledged. The work in Zagreb (I.A., Z.G., and M.E.M.) has been supported by the Ministry of Science and Technology of Croatia through project 00980801 and HR-US project JF 143. ",

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T1 - On the acidity of cyclopropanaphthalenes

T2 - Gas phase and computational studies

AU - Antol, Ivana

AU - Glasovac, Zoran

AU - Hare, Michael C.

AU - Eckert-Maksic, Mirjana

AU - Kass, Steven R.

N1 - Funding Information: Support from the National Science Foundation, the donors of the Petroleum Research Foundation, as administered by the American Chemical Society, the Minnesota Supercomputer Institute, and the University of Minnesota-IBM Shared Research Project are gratefully acknowledged. The work in Zagreb (I.A., Z.G., and M.E.M.) has been supported by the Ministry of Science and Technology of Croatia through project 00980801 and HR-US project JF 143.

PY - 2003/1/1

Y1 - 2003/1/1

N2 - 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 (ΔG°acid=357.5±2.1kcal mol-1 (3H) and 365.2±2.1kcal mol-1 (6H), ΔH°acid=365.1±2.1kcal mol-1 (3H) and 372.7±2.1kcal mol-1 (6H)). These results were modeled by MP2 and BVWN5 calculations, and additional computations were carried out on benzocyclopropene (1H), toluene (2H), 1H-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.

AB - 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 (ΔG°acid=357.5±2.1kcal mol-1 (3H) and 365.2±2.1kcal mol-1 (6H), ΔH°acid=365.1±2.1kcal mol-1 (3H) and 372.7±2.1kcal mol-1 (6H)). These results were modeled by MP2 and BVWN5 calculations, and additional computations were carried out on benzocyclopropene (1H), toluene (2H), 1H-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.

KW - Ab initio

KW - Antiaromaticity

KW - Aromaticity

KW - Cycloproparenes

KW - DFT calculations

KW - FTMS

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ER -

On the acidity of cyclopropanaphthalenes: Gas phase and computational studies

Abstract

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Keywords

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