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1H-Cyclopropa[b]naphthalene


Gas phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas104.kcal/molCcbBillups, Chow, et al., 1973 

Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafsolid86.0 ± 0.2kcal/molCcbBillups, Chow, et al., 1973 
Quantity Value Units Method Reference Comment
Deltacsolid-1393.8 ± 0.2kcal/molCcbBillups, Chow, et al., 1973Corresponding «DELTA»fsolid = 86.0 kcal/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Deltasub18.kcal/molEBillups, Chow, et al., 1973ALS
Deltasub17.9kcal/molN/ABillups, Chow, et al., 1973DRB

Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C11H7- + Hydrogen cation = 1H-Cyclopropa[b]naphthalene

By formula: C11H7- + H+ = C11H8

Quantity Value Units Method Reference Comment
Deltar365.0 ± 2.2kcal/molG+TSAntol, Glasovac, et al., 2003gas phase; B
Quantity Value Units Method Reference Comment
Deltar357.5 ± 2.1kcal/molIMREAntol, Glasovac, et al., 2003gas phase; B

1H-Cyclopropa[b]naphthalene + Methyl Alcohol = Naphthalene, 2-(methoxymethyl)-

By formula: C11H8 + CH4O = C12H12O

Quantity Value Units Method Reference Comment
Deltar-47.43 ± 0.12kcal/molCmBillups, Chow, et al., 1973liquid phase; solvent: Methanol; ALS

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV) Method Reference Comment
8.03PESchulz, Schweig, et al., 1980LLK
8.12PELecoultre, Heilbronner, et al., 1988Vertical value; LL

De-protonation reactions

C11H7- + Hydrogen cation = 1H-Cyclopropa[b]naphthalene

By formula: C11H7- + H+ = C11H8

Quantity Value Units Method Reference Comment
Deltar365.0 ± 2.2kcal/molG+TSAntol, Glasovac, et al., 2003gas phase; B
Quantity Value Units Method Reference Comment
Deltar357.5 ± 2.1kcal/molIMREAntol, Glasovac, et al., 2003gas phase; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Billups, Chow, et al., 1973
Billups, W.E.; Chow, W.Y.; Leavell, K.H.; Lewis, E.S.; Margrave, J.L.; Sass, R.L.; Shieh, J.J.; Werness, P.G.; Wood, J.L., Structure and thermochemistry of benzocyclopropenes. Bond fixation and strain energy, J. Am. Chem. Soc., 1973, 95, 7878-7880. [all data]

Antol, Glasovac, et al., 2003
Antol, I.; Glasovac, Z.; Hare, M.C.; Eckert-Maksic, M.; Kass, S.R., On the acidity of cyclopropanaphthalenes - Gas phase and computational studies, Int. J. Mass Spectrom., 2003, 222, 1-3, 11-26, https://doi.org/10.1016/S1387-3806(02)00953-3 . [all data]

Schulz, Schweig, et al., 1980
Schulz, R.; Schweig, A.; Wentrup, C.; Winter, H.-W., 2-Vinylidene-2H-indene, Angew. Chem. Int. Ed. Engl., 1980, 19, 821. [all data]

Lecoultre, Heilbronner, et al., 1988
Lecoultre, J.; Heilbronner, E.; Muller, P.; Rodriguez, D., The influence of fluoro substituents on cyclopropa, -benzene, -naphthalene, and -anthracene, Collect. Czech. Chem. Commun., 1988, 53, 2385. [all data]


Notes

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