Methenamine
- Formula: C6H12N4
- Molecular weight: 140.1863
- IUPAC Standard InChI: InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2
- IUPAC Standard InChIKey: VKYKSIONXSXAKP-UHFFFAOYSA-N
- CAS Registry Number: 100-97-0
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: 1,3,5,7-Tetraazaadamantane; 1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane; Hexamethylenetetramine; Aceto HMT; Aminoform; Aminoformaldehyde; Ammoform; Ammonioformaldehyde; Antihydral; Cystogen; Duirexol; Ekagom H; Formamine; Formin; Herax UTS; Heterin; Hexa-Flo-Pulver; Hexaform; Hexamine; Hexasan; Methenamin; Preparation AF; Uramin; Uratrine; Uritone; Urodeine; Urotropin; Urotropine; Xametrin; 1,3,5,7-Tetraazatricyclo-[3.3.1.1(3,7)]decane; Cystamin; Hexaloids; Hexamethylenetetraamine; Hexamethylentetramin; Hexilmethylenamine; Resotropin; Nocceler H; Vulkacit H 30; Hexa; H.M.T.; HMT; Metramine; Vesaloin; Formin (heterocycle); Hexamethylenamine; Hexamine (heterocycle); Sanceler H
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References, Notes
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 |
|---|---|---|---|---|---|
| ΔfH°gas | 47.6 ± 0.7 | kcal/mol | Ccr | Mansson, Rapport, et al., 1970 | ALS |
| ΔfH°gas | 47.30 | kcal/mol | N/A | Delepine and Badoche, 1942 | Value computed using ΔfHsolid° value of 123.0 kj/mol from Delepine and Badoche, 1942 and ΔsubH° value of 74.9 kj/mol from Mansson, Rapport, et al., 1970.; DRB |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, References, Notes
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | 29.65 ± 0.18 | kcal/mol | Ccr | Mansson, Rapport, et al., 1970 | ALS |
| ΔfH°solid | 29.40 | kcal/mol | Ccb | Delepine and Badoche, 1942 | Author's hf298_condensed=27.10 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1003.85 ± 0.16 | kcal/mol | Ccr | Mansson, Rapport, et al., 1970 | ALS |
| ΔcH°solid | -1003.6 | kcal/mol | Ccb | Delepine and Badoche, 1942 | Author's hf298_condensed=27.10 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 39.049 | cal/mol*K | N/A | Westrum, 1961 | DH |
| S°solid,1 bar | 39.049 | cal/mol*K | N/A | Chang and Westrum, 1960 | DH |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 36.398 | 298.15 | Westrum, 1961 | T = 5 to 350 K. Only value at 298.15 K given.; DH |
| 36.398 | 298.15 | Chang and Westrum, 1960 | T = 5 to 350 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References, Notes
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:
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔsubH° | 19.0 ± 0.1 | kcal/mol | GS | Verevkin, 2002 | Based on data from 339. to 378. K.; AC |
| ΔsubH° | 17.9 ± 0.7 | kcal/mol | V | Mansson, Rapport, et al., 1970 | ALS |
| ΔsubH° | 17.9 | kcal/mol | N/A | Mansson, Rapport, et al., 1970 | DRB |
| ΔsubH° | 17.9 ± 0.69 | kcal/mol | N/A | Wada, Kishida, et al., 1960 | See also Westrum, Mansson, et al., 1970.; AC |
Enthalpy of sublimation
| ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 18.6 ± 0.1 | 359. | GS | Verevkin, 2002 | Based on data from 339. to 378. K.; AC |
| 18.4 | 313. | A | Stephenson and Malanowski, 1987 | Based on data from 298. to 453. K.; AC |
| 18.8 | 316. | TE,ME | De Wit, Van Miltenburg, et al., 1983 | Based on data from 302. to 328. K.; AC |
| 17.7 ± 0.2 | 289. | TE | Budurov, 1960 | Based on data from 281. to 298. K.; AC |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References, Notes
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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.26 | PE | Dewar and Worley, 1969 | RDSH |
| 8.55 | PE | Cowley, Lattman, et al., 1982 | Vertical value; LBLHLM |
| 8.53 | PE | Nelsen and Buschek, 1974 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.
Mansson, Rapport, et al., 1970
Mansson, M.; Rapport, N.; Westrum, E.F., Jr.,
Enthalpies of formation of globular molecules. I. Adamantane and hexamethylenetetramine,
J. Am. Chem. Soc., 1970, 92, 7296-7299. [all data]
Delepine and Badoche, 1942
Delepine, M.; Badoche, M.,
Thermochimie de l'aldehyde formique, de l'hexamethylene-tetramine et de ses derive,
C. R. Acad. Sci. Paris, 1942, 214, 777-780. [all data]
Westrum, 1961
Westrum, E.F., Jr.,
The thermophysical properties of three globular molecules,
J. Phys. Chem. Solids, 1961, 18, 83-85. [all data]
Chang and Westrum, 1960
Chang, S.-S.; Westrum, E.F., Jr.,
Heat capacities and thermodynamic properties of globular molecules. I. Adamantane and hexamethylenetetramine,
J. Phys. Chem., 1960, 64, 1547-1551. [all data]
Verevkin, 2002
Verevkin, Sergey P.,
Relationships among strain energies of mono- and poly-cyclic cyclohexanoid molecules and strain of their component rings,
The Journal of Chemical Thermodynamics, 2002, 34, 2, 263-275, https://doi.org/10.1006/jcht.2001.0896
. [all data]
Wada, Kishida, et al., 1960
Wada, Tadayoshi; Kishida, Etsuko; Tomiie, Yujiro; Suga, Hiroshi; Seki, Syûzô; Nitta, Isamu,
Crystal Structure and Thermodynamical Investigations of Triethylenediamine, C6H12N2,
Bull. Chem. Soc. Jpn., 1960, 33, 9, 1317-1318, https://doi.org/10.1246/bcsj.33.1317
. [all data]
Westrum, Mansson, et al., 1970
Westrum, Edgar F.; Mansson, Margret.; Rapport, Naomi.,
Enthalpies of formation of globular molecules. I. Adamantane and hexamethylenetetramine,
J. Am. Chem. Soc., 1970, 92, 25, 7296-7299, https://doi.org/10.1021/ja00728a011
. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G.,
Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation,
The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4
. [all data]
Budurov, 1960
Budurov, S.,
Izv. Khim. Inst. Bulg. Akad. Nauk, 1960, 7, 281. [all data]
Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation,
J. Chem. Phys., 1969, 50, 654. [all data]
Cowley, Lattman, et al., 1982
Cowley, A.H.; Lattman, M.; Stricklen, P.M.; Verkade, J.G.,
UV photoelectron spectroscopic investigation of some polycyclic group 5A compounds and related acyclic species. 1. Free and coordinated aminophosphines and related compounds,
Inorg. Chem., 1982, 21, 543. [all data]
Nelsen and Buschek, 1974
Nelsen, S.F.; Buschek, J.M.,
Photoelectron spectra of some cyclic di- and polyamines. Lone pair-lone pair interaction in 1,3- and 1,4-diamines,
J. Am. Chem. Soc., 1974, 96, 7930. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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