Benzene, nitro- anion

Formula: C₆H₅NO₂^-
Molecular weight: 123.1099
CAS Registry Number: 12169-65-2
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Gas phase thermochemistry data

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Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-7.1 ± 2.3	kcal/mol	R-EA	Chowdhury, Heinis, et al., 1986	ΔGea(423 K) = -22.8 kcal/mol; ΔSea = -1.0 eu.

Reaction thermochemistry data

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Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + CH₄O = (C₆H₅NO₂^- • CH₄O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	15.10 ± 0.20	kcal/mol	TDAs	Sieck, 1985	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	26.1	cal/mol*K	PHPMS	Sieck, 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	7.30 ± 0.40	kcal/mol	TDAs	Sieck, 1985	gas phase; B
Δ_rG°	6.3 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 70°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
6.3	343.	PHPMS	Chowdhury, 1987	gas phase; M

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₂H₆OS = (C₆H₅NO₂^- • C₂H₆OS)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	16.80 ± 0.10	kcal/mol	TDAs	Sieck, 1985	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	24.5	cal/mol*K	PHPMS	Sieck, 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	9.50 ± 0.20	kcal/mol	TDAs	Sieck, 1985	gas phase; B
Δ_rG°	8.6 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 70°C.; B

(C₆H₅NO₂^- • ) + = (C₆H₅NO₂^- • 2)

By formula: (C₆H₅NO₂^- • H₂O) + H₂O = (C₆H₅NO₂^- • 2H₂O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	12.40 ± 0.10	kcal/mol	TDAs	Sieck, 1985	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	24.7	cal/mol*K	PHPMS	Sieck, 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	5.00 ± 0.40	kcal/mol	TDAs	Sieck, 1985	gas phase; B

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + H₂O = (C₆H₅NO₂^- • H₂O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	13.50 ± 0.10	kcal/mol	TDAs	Sieck, 1985	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	21.9	cal/mol*K	PHPMS	Sieck, 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	7.00 ± 0.20	kcal/mol	TDAs	Sieck, 1985	gas phase; B

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₂H₄O₂ = (C₆H₅NO₂^- • C₂H₄O₂)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	22.60 ± 0.10	kcal/mol	TDAs	Sieck, 1985	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	26.8	cal/mol*K	PHPMS	Sieck, 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	14.60 ± 0.20	kcal/mol	TDAs	Sieck, 1985	gas phase; B

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₃H₆O = (C₆H₅NO₂^- • C₃H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	14.20 ± 0.20	kcal/mol	TDAs	Sieck, 1985	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	26.3	cal/mol*K	PHPMS	Sieck, 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	6.40 ± 0.40	kcal/mol	TDAs	Sieck, 1985	gas phase; B

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₄H₈O = (C₆H₅NO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	3.2 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
3.2	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₃H₇NO = (C₆H₅NO₂^- • C₃H₇NO)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	6.2 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 70°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
6.2	343.	PHPMS	Chowdhury, 1987	gas phase; M

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₂H₃N = (C₆H₅NO₂^- • C₂H₃N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	6.6 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 70°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
6.6	343.	PHPMS	Chowdhury, 1987	gas phase; M

C₆H₅NO₂^- + = C₆H₅F₄NO₂Si^-

By formula: C₆H₅NO₂^- + F₄Si = C₆H₅F₄NO₂Si^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	35.0 ± 2.0	kcal/mol	TDAs	Williamson, Knighton, et al., 2001	gas phase; at 150 C; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	15.50 ± 0.60	kcal/mol	TDAs	Williamson, Knighton, et al., 2001	gas phase; at 150 C; B

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₄H₁₀O = (C₆H₅NO₂^- • C₄H₁₀O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	16.4	kcal/mol	PHPMS	Sieck, 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	27.2	cal/mol*K	PHPMS	Sieck, 1985	gas phase; M

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, References, Notes

Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + CH₄O = (C₆H₅NO₂^- • CH₄O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	15.10 ± 0.20	kcal/mol	TDAs	Sieck, 1985	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	26.1	cal/mol*K	PHPMS	Sieck, 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	7.30 ± 0.40	kcal/mol	TDAs	Sieck, 1985	gas phase; B
Δ_rG°	6.3 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 70°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
6.3	343.	PHPMS	Chowdhury, 1987	gas phase; M

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₂H₃N = (C₆H₅NO₂^- • C₂H₃N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	6.6 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 70°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
6.6	343.	PHPMS	Chowdhury, 1987	gas phase; M

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₂H₄O₂ = (C₆H₅NO₂^- • C₂H₄O₂)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	22.60 ± 0.10	kcal/mol	TDAs	Sieck, 1985	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	26.8	cal/mol*K	PHPMS	Sieck, 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	14.60 ± 0.20	kcal/mol	TDAs	Sieck, 1985	gas phase; B

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₂H₆OS = (C₆H₅NO₂^- • C₂H₆OS)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	16.80 ± 0.10	kcal/mol	TDAs	Sieck, 1985	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	24.5	cal/mol*K	PHPMS	Sieck, 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	9.50 ± 0.20	kcal/mol	TDAs	Sieck, 1985	gas phase; B
Δ_rG°	8.6 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 70°C.; B

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₃H₆O = (C₆H₅NO₂^- • C₃H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	14.20 ± 0.20	kcal/mol	TDAs	Sieck, 1985	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	26.3	cal/mol*K	PHPMS	Sieck, 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	6.40 ± 0.40	kcal/mol	TDAs	Sieck, 1985	gas phase; B

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₃H₇NO = (C₆H₅NO₂^- • C₃H₇NO)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	6.2 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 70°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
6.2	343.	PHPMS	Chowdhury, 1987	gas phase; M

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₄H₈O = (C₆H₅NO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	3.2 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
3.2	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₄H₁₀O = (C₆H₅NO₂^- • C₄H₁₀O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	16.4	kcal/mol	PHPMS	Sieck, 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	27.2	cal/mol*K	PHPMS	Sieck, 1985	gas phase; M

C₆H₅NO₂^- + = C₆H₅F₄NO₂Si^-

By formula: C₆H₅NO₂^- + F₄Si = C₆H₅F₄NO₂Si^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	35.0 ± 2.0	kcal/mol	TDAs	Williamson, Knighton, et al., 2001	gas phase; at 150 C; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	15.50 ± 0.60	kcal/mol	TDAs	Williamson, Knighton, et al., 2001	gas phase; at 150 C; B

C₆H₅NO₂^- + = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + H₂O = (C₆H₅NO₂^- • H₂O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	13.50 ± 0.10	kcal/mol	TDAs	Sieck, 1985	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	21.9	cal/mol*K	PHPMS	Sieck, 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	7.00 ± 0.20	kcal/mol	TDAs	Sieck, 1985	gas phase; B

(C₆H₅NO₂^- • ) + = (C₆H₅NO₂^- • 2)

By formula: (C₆H₅NO₂^- • H₂O) + H₂O = (C₆H₅NO₂^- • 2H₂O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	12.40 ± 0.10	kcal/mol	TDAs	Sieck, 1985	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	24.7	cal/mol*K	PHPMS	Sieck, 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	5.00 ± 0.40	kcal/mol	TDAs	Sieck, 1985	gas phase; B

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Ion clustering data, Notes

Chowdhury, Heinis, et al., 1986
Chowdhury, S.; Heinis, T.; Grimsrud, E.P.; Kebarle, P., Entropy Changes and Electron Affinities from Gas-Phase Electron Transfer Equilibria: A^- + B = A + B^-, J. Phys. Chem., 1986, 90, 12, 2747, https://doi.org/10.1021/j100403a037 . [all data]

Sieck, 1985
Sieck, L.W., Thermochemistry of Solvation of NO₂^- and C₆H₅NO₂^- by Polar Molecules in the Vapor Phase. Comparison with Cl^- and Variation with Ligand Structure., J. Phys. Chem., 1985, 89, 25, 5552, https://doi.org/10.1021/j100271a049 . [all data]

Chowdhury, Grimsrud, et al., 1987
Chowdhury, S.; Grimsrud, E.P.; Kebarle, P., Bonding of Charged Delocalized Anions to Protic and Dipolar Aprotic Solvent Molecules, J. Phys. Chem., 1987, 91, 10, 2551, https://doi.org/10.1021/j100294a021 . [all data]

Chowdhury, 1987
Chowdhury, S. Grimsrud, Bonding of Charge Delocalized Anions to Protic and Dipolar Aprotic Solvents, J. Phys. Chem., 1987, 91, 10, 2551, https://doi.org/10.1021/j100294a021 . [all data]

Williamson, Knighton, et al., 2001
Williamson, D.H.; Knighton, W.B.; Grimsrud, E.P., Lewis acid-base interactions of SiF4 with molecular anions formed by electron capture reactions, Int. J. Mass Spectrom., 2001, 206, 1-2, 53-61, https://doi.org/10.1016/S1387-3806(00)00388-2 . [all data]

Notes

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Symbols used in this document:

T	Temperature
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_rS°	Entropy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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