Cyclohexanamine, protonated

Formula: C₆H₁₄N⁺
Molecular weight: 100.1815
Information on this page:
Options:
- Switch to SI units

Reaction thermochemistry data

Go To: Top, Ion clustering data, References, Notes

Data compiled by: 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

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₁₂H₂₄O₆ = (C₆H₁₄N⁺ • C₁₂H₂₄O₆)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	48. ± 4.	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase; Entropy change calculated or estimated
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	38.	cal/mol*K	N/A	Meot-Ner (Mautner), 1983	gas phase; Entropy change calculated or estimated

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
23.	670.	PHPMS	Meot-Ner (Mautner), 1983	gas phase; Entropy change calculated or estimated

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₄H₁₀O = (C₆H₁₄N⁺ • C₄H₁₀O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	22.0	kcal/mol	PHPMS	Meot-Ner, 1984	gas phase
Δ_rH°	21.9	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	31.8	cal/mol*K	PHPMS	Meot-Ner, 1984	gas phase
Δ_rS°	31.9	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1983	gas phase

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₈H₁₈O₄ = (C₆H₁₄N⁺ • C₈H₁₈O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	43.3	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase; triglyme
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	43.8	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1983	gas phase; triglyme

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₆H₁₄O₃ = (C₆H₁₄N⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	39.7	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase; diglyme
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	44.6	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1983	gas phase; diglyme

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₅H₁₂O₂ = (C₆H₁₄N⁺ • C₅H₁₂O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	28.4	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	35.0	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1983	gas phase

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₁₀H₂₀O₅ = (C₆H₁₄N⁺ • C₁₀H₂₀O₅)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	42.3	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	36.5	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1983	gas phase

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₄H₁₀O₂ = (C₆H₁₄N⁺ • C₄H₁₀O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	29.4	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	35.5	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1983	gas phase

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₈H₁₆O₄ = (C₆H₁₄N⁺ • C₈H₁₆O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	37.2	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	34.8	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1983	gas phase

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₆H₁₄O = (C₆H₁₄N⁺ • C₆H₁₄O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	25.4	kcal/mol	PHPMS	Meot-Ner, 1984	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	31.2	cal/mol*K	PHPMS	Meot-Ner, 1984	gas phase

(C₆H₁₄N⁺ • ) + = (C₆H₁₄N⁺ • 2)

By formula: (C₆H₁₄N⁺ • C₆H₁₁NO₃) + C₆H₁₁NO₃ = (C₆H₁₄N⁺ • 2C₆H₁₁NO₃)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	20.4	kcal/mol	PHPMS	Meot-Ner (Mautner), 1988	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	29.5	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1988	gas phase

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₆H₁₁NO₃ = (C₆H₁₄N⁺ • C₆H₁₁NO₃)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	37.8	kcal/mol	PHPMS	Meot-Ner (Mautner), 1988	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	40.9	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1988	gas phase

Ion clustering data

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

Data compiled by: 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

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₄H₁₀O = (C₆H₁₄N⁺ • C₄H₁₀O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	22.0	kcal/mol	PHPMS	Meot-Ner, 1984	gas phase
Δ_rH°	21.9	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	31.8	cal/mol*K	PHPMS	Meot-Ner, 1984	gas phase
Δ_rS°	31.9	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1983	gas phase

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₄H₁₀O₂ = (C₆H₁₄N⁺ • C₄H₁₀O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	29.4	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	35.5	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1983	gas phase

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₅H₁₂O₂ = (C₆H₁₄N⁺ • C₅H₁₂O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	28.4	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	35.0	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1983	gas phase

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₆H₁₁NO₃ = (C₆H₁₄N⁺ • C₆H₁₁NO₃)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	37.8	kcal/mol	PHPMS	Meot-Ner (Mautner), 1988	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	40.9	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1988	gas phase

(C₆H₁₄N⁺ • ) + = (C₆H₁₄N⁺ • 2)

By formula: (C₆H₁₄N⁺ • C₆H₁₁NO₃) + C₆H₁₁NO₃ = (C₆H₁₄N⁺ • 2C₆H₁₁NO₃)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	20.4	kcal/mol	PHPMS	Meot-Ner (Mautner), 1988	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	29.5	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1988	gas phase

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₆H₁₄O = (C₆H₁₄N⁺ • C₆H₁₄O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	25.4	kcal/mol	PHPMS	Meot-Ner, 1984	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	31.2	cal/mol*K	PHPMS	Meot-Ner, 1984	gas phase

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₆H₁₄O₃ = (C₆H₁₄N⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	39.7	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase; diglyme
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	44.6	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1983	gas phase; diglyme

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₈H₁₆O₄ = (C₆H₁₄N⁺ • C₈H₁₆O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	37.2	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	34.8	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1983	gas phase

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₈H₁₈O₄ = (C₆H₁₄N⁺ • C₈H₁₈O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	43.3	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase; triglyme
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	43.8	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1983	gas phase; triglyme

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₁₀H₂₀O₅ = (C₆H₁₄N⁺ • C₁₀H₂₀O₅)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	42.3	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	36.5	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1983	gas phase

C₆H₁₄N⁺ + = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₁₂H₂₄O₆ = (C₆H₁₄N⁺ • C₁₂H₂₄O₆)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	48. ± 4.	kcal/mol	PHPMS	Meot-Ner (Mautner), 1983	gas phase; Entropy change calculated or estimated
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	38.	cal/mol*K	N/A	Meot-Ner (Mautner), 1983	gas phase; Entropy change calculated or estimated

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
23.	670.	PHPMS	Meot-Ner (Mautner), 1983	gas phase; Entropy change calculated or estimated

References

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

Meot-Ner (Mautner), 1983
Meot-Ner (Mautner), M., The Ionic Hydrogen Bond. 3. Multiple and -CH+...O- Bonds. Complexes of Ammonium Ions with Polyethers and Crown Ethers, J. Am. Chem. Soc., 1983, 105, 15, 4912, https://doi.org/10.1021/ja00353a012 . [all data]

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

Meot-Ner (Mautner), 1988
Meot-Ner (Mautner), M., Models for Strong Interactions in Proteins and Enzymes. 2. Interactions of Ions with the Peptide Link and Imidazole, J. Am. Chem. Soc., 1988, 110, 10, 3075, https://doi.org/10.1021/ja00218a014 . [all data]

Notes

Go To: Top, Reaction thermochemistry data, Ion clustering data, References

Symbols used in this document:

T Temperature

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
The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
Customer support for NIST Standard Reference Data products.

T	Temperature
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