Cyclopentanol
- Formula: C5H10O
- Molecular weight: 86.1323
- IUPAC Standard InChIKey: XCIXKGXIYUWCLL-UHFFFAOYSA-N
- CAS Registry Number: 96-41-3
- 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: Cyclopentyl alcohol; Hydroxycyclopentane; UN 2244
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Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -243.0 | kJ/mol | N/A | Wiberg, Wasserman, et al., 1985 | Value computed using ΔfHliquid° value of -300.4±1.0 kj/mol from Wiberg, Wasserman, et al., 1985 and ΔvapH° value of 57.4 kj/mol from Sellers and Sunner, 1962.; DRB |
ΔfH°gas | -242.6 ± 1.7 | kJ/mol | Ccb | Sellers and Sunner, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = -241.1 kJ/mol; ALS |
ΔfH°gas | -242.9 | kJ/mol | N/A | Parks, Mosley, et al., 1950 | Value computed using ΔfHliquid° value of -300.3±0.2 kj/mol from Parks, Mosley, et al., 1950 and ΔvapH° value of 57.4 kj/mol from Sellers and Sunner, 1962.; DRB |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
105.43 | 298.15 | Kabo G.J., 1995 | Selected thermodynamic functions were calculated so that statistical entropy value at 340 K was put into agreement with the experimental one by adjusting the pseudorotational moment of inertia. Statistically calculated S(T) and Cp(T) values given in [ Thermodynamics Research Center, 1997] are 2-13 and 7-9 J/mol*K, respectively, larger than those of [ Kabo G.J., 1995].; GT |
106.09 | 300. | ||
142.01 | 400. | ||
174.02 | 500. | ||
200.71 | 600. | ||
222.75 | 700. | ||
241.29 | 800. | ||
257.00 | 900. | ||
270.39 | 1000. |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
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
C5H9O- + =
By formula: C5H9O- + H+ = C5H10O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1602. ± 19. | kJ/mol | D-EA | Alconcel and Continetti, 2002 | gas phase; derived acidity seems ca. 10 kcal/mol too weak, and EA likewise; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1535. ± 4.6 | kJ/mol | N/A | Garver, Yang, et al., 2011 | gas phase; B |
ΔrG° | 1569. ± 20. | kJ/mol | H-TS | Alconcel and Continetti, 2002 | gas phase; derived acidity seems ca. 10 kcal/mol too weak, and EA likewise; B |
By formula: C5H8O + H2 = C5H10O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -60.25 ± 0.67 | kJ/mol | Cm | Wiberg, Crocker, et al., 1991 | liquid phase; ALS |
ΔrH° | -51.25 ± 0.63 | kJ/mol | Chyd | Conn, Kistiakowsky, et al., 1939 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -52.3 ± 0.3 kJ/mol; At 355 K; ALS |
By formula: C4F6O3 + C5H10O = C7H9F3O2 + C2HF3O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -92.96 ± 0.23 | kJ/mol | Cac | Wiberg, Wasserman, et al., 1985 | liquid phase; solvent: Trifluoroactic acid; Trifluoroacetolysis; ALS |
By formula: C5H10O = C5H8O + H2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 54.9 ± 4.7 | kJ/mol | Eqk | Fedoseenko, Yursha, et al., 1984 | gas phase; ALS |
ΔrH° | 51.30 | kJ/mol | Eqk | Cubberley and Mueller, 1946 | gas phase; ALS |
By formula: C6H10O + C5H10O = C6H12O + C5H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -11.6 ± 1.7 | kJ/mol | Eqk | Fedoseenko, Yursha, et al., 1984 | gas phase; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
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
View reactions leading to C5H10O+ (ion structure unspecified)
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
798. ± 6. | Cao and Holmes, 2001 | MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.72 | PI | Traeger, 1985 | LBLHLM |
9.58 ± 0.06 | EI | Holmes, Yuan, et al., 1977 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H5O+ | 9.72 | C2H5 | PI | Traeger, 1985 | LBLHLM |
C3H6O+ | 9.98 | C2H4 | EI | Holmes and Lossing, 1980 | LLK |
C5H8+ | 9.66 ± 0.06 | H2O | EI | Holmes, Yuan, et al., 1977 | LLK |
C5H8+ | 9.49 | H2O | EI | Lewis and Hamill, 1970 | RDSH |
H2O+ | 13.23 | C5H8 | EI | Lewis and Hamill, 1970 | RDSH |
De-protonation reactions
C5H9O- + =
By formula: C5H9O- + H+ = C5H10O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1602. ± 19. | kJ/mol | D-EA | Alconcel and Continetti, 2002 | gas phase; derived acidity seems ca. 10 kcal/mol too weak, and EA likewise; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1535. ± 4.6 | kJ/mol | N/A | Garver, Yang, et al., 2011 | gas phase; B |
ΔrG° | 1569. ± 20. | kJ/mol | H-TS | Alconcel and Continetti, 2002 | gas phase; derived acidity seems ca. 10 kcal/mol too weak, and EA likewise; B |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-1501 |
NIST MS number | 233847 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | SE-30 | 100. | 792. | Winskowski, 1983 | Gaschrom Q; Column length: 2. m |
Packed | Apiezon L | 120. | 768. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | Apiezon L | 160. | 781. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | Apiezon L | 130. | 768. | Bogoslovsky, Anvaer, et al., 1978 | |
Packed | DC-200 | 100. | 782. | Rohrschneider, 1966 | Column length: 4. m |
Packed | Apiezon L | 100. | 767. | Rohrschneider, 1966 | Column length: 5. m |
Packed | Apiezon L | 130. | 768. | Wehrli and Kováts, 1959 | Celite; Column length: 2.25 m |
Packed | Apiezon L | 190. | 773. | Wehrli and Kováts, 1959 | Celite; Column length: 2.25 m |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Carbowax 20M | 100. | 1298. | Rohrschneider, 1966 | Column length: 2. m |
Kovats' RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1283. | Nishimura, Yamaguchi, et al., 1989 | 2. K/min; Column length: 50. m; Column diameter: 0.22 mm; Tstart: 80. C; Tend: 200. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 765. | Boulanger, Chassagne, et al., 1999 | 30. m/0.25 mm/0.25 μm, H2; Program: 40C(5min) => 2C/min => 220C => 5C/min => 250C(15min) |
Capillary | DB-5 | 781. | Boulanger, Chassagne, et al., 1999 | 30. m/0.25 mm/0.25 μm, H2; Program: 40C(5min) => 2C/min => 220C => 5C/min => 250C(15min) |
Capillary | DB-5 | 765. | Boulanger, Chassagne, et al., 1999 | 30. m/0.25 mm/0.25 μm, H2; Program: 40C(5min) => 2C/min => 220C => 5C/min => 250C(15min) |
Capillary | DB-5 | 781. | Boulanger, Chassagne, et al., 1999 | 30. m/0.25 mm/0.25 μm, H2; Program: 40C(5min) => 2C/min => 220C => 5C/min => 250C(15min) |
Capillary | Methyl Silicone | 774. | Peng, Yang, et al., 1991 | Program: not specified |
Packed | SE-30 | 774. | Peng, Ding, et al., 1988 | Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1300. | Fernandez-Segovia, Escriche, et al., 2006 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 10. K/min, 230. C @ 25. min |
Capillary | Supelcowax-10 | 1314. | Chung, Yung, et al., 2002 | 60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min |
Capillary | Supelcowax-10 | 1314. | Chung, Yung, et al., 2001 | 60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min |
Capillary | DB-Wax | 1309. | Beauchene, Grua-Priol, et al., 2000 | 60. m/0.32 mm/0.5 μm, He, 3. K/min, 160. C @ 5. min; Tstart: 30. C |
Capillary | DB-Wax | 1323. | Iwaoka, Hagi, et al., 1994 | He, 40. C @ 5. min, 2. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tend: 200. C |
Capillary | DB-Wax | 1278. | Fröhlich, Duque, et al., 1989 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; Tend: 250. C |
Capillary | DB-Wax | 1281. | Fröhlich, Duque, et al., 1989 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; Tend: 250. C |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apieson L | 120. | 795. | Kurdina, Markovich, et al., 1969 | not specified, not specified |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 802. | Anker, Jurs, et al., 1990 | 2. K/min; Column length: 50. m; Column diameter: 0.28 mm; Tstart: 80. C; Tend: 200. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-30 | 805. | Vinogradov, 2004 | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 792. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | ZB-Wax | 1328. | Wierda R.L., Fletcher G., et al., 2006 | 60. m/0.32 mm/0.5 μm, He, 40. C @ 2. min, 3. K/min, 250. C @ 10. min |
Capillary | DB-Wax | 1300. | Fu, Yoon, et al., 2002 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 8. K/min, 250. C @ 5. min |
Capillary | TC-Wax | 1290. | Fukami, Ishiyama, et al., 2002 | 60. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 50. C; Tend: 230. C |
Capillary | DB-Wax | 1303. | Umano, Nakahara, et al., 1999 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 2. min, 2. K/min; Tend: 200. C |
Capillary | Carbowax 20M | 1283. | Anker, Jurs, et al., 1990 | 2. K/min; Column length: 80. m; Column diameter: 0.2 mm; Tstart: 70. C; Tend: 170. C |
Capillary | Carbowax 20M | 1289. | Mihara, Tateba, et al., 1988 | N2, 3. K/min; Column length: 50. m; Column diameter: 0.22 mm; Tstart: 80. C; Tend: 200. C |
Capillary | Carbowax 20M | 1292. | Mihara, Tateba, et al., 1988 | N2, 3. K/min; Column length: 50. m; Column diameter: 0.22 mm; Tstart: 80. C; Tend: 200. C |
Capillary | Carbowax 20M | 1289. | Mihara, Tateba, et al., 1987 | N2, 3. K/min; Column length: 50. m; Column diameter: 0.22 mm; Tstart: 80. C; Tend: 200. C |
Capillary | Carbowax 20M | 1292. | Mihara, Tateba, et al., 1987 | N2, 3. K/min; Column length: 50. m; Column diameter: 0.22 mm; Tstart: 80. C; Tend: 200. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1323. | Sampaio, Garruti, et al., 2011 | 30. m/0.25 mm/0.25 μm, Hydrogen; Program: 35 0C (9 min) 5 0C/min -> 80 0C 1 0C/min -> 100 0C 16 0C/min -> 210 0C (20 min) |
Capillary | DB-Wax | 1339. | Yongsheng, Hua, et al., 2008 | 30. m/0.32 mm/0.25 μm, Helium; Program: 40 0C (4 min) 3 0C/min -> 50 0C 5 0C/min -> 120 0C 7 0C/min -> 175 0C 10 0C/min -> 230 0C (8 min) |
Capillary | HP-Innowax | 1280. | Quijano and Pino, 2006 | 60. m/0.25 mm/0.25 μm, Nitrogen; Program: 50 0C (4 min) -> 40 0C 4 0C/min -> 220 0C |
Capillary | Carbowax 20M | 1283. | Vinogradov, 2004 | Program: not specified |
Capillary | DB-Wax | 1327. | Piveteau, le Guen, et al., 2000 | 60. m/0.32 mm/0.5 μm, He; Program: 50C(6min) => 1C/min => 130C => 10C/min => 240C (15min) |
Capillary | DB-Wax | 1297. | Peng, Yang, et al., 1991, 2 | Program: not specified |
Capillary | DB-Wax | 1327. | Peng, Yang, et al., 1991, 2 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Wiberg, Wasserman, et al., 1985
Wiberg, K.B.; Wasserman, D.J.; Martin, E.J.; Murcko, M.A.,
Enthalpies of hydration of alkenes. 3. Cycloalkenes,
J. Am. Chem. Soc., 1985, 107, 6019-6022. [all data]
Sellers and Sunner, 1962
Sellers, P.; Sunner, S.,
Heats of combustion of cyclic ketones and alcohols,
Acta Chem. Scand., 1962, 16, 46-52. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Parks, Mosley, et al., 1950
Parks, G.S.; Mosley, J.R.; Peterson, P.V., Jr.,
Heats of combustion and formation of some organic compounds containing oxygen,
J. Chem. Phys., 1950, 18, 152. [all data]
Kabo G.J., 1995
Kabo G.J.,
Thermodynamic properties, conformation, and phase transitions of cyclopentanol,
J. Chem. Thermodyn., 1995, 27, 953-967. [all data]
Thermodynamics Research Center, 1997
Thermodynamics Research Center,
Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]
Alconcel and Continetti, 2002
Alconcel, L.S.; Continetti, R.E.,
Dissociation dynamics and stability of cyclopentoxy and cyclopentoxide,
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. [all data]
Garver, Yang, et al., 2011
Garver, J.M.; Yang, Z.B.; Kato, S.; Wren, S.W.; Vogelhuber, K.M.; Lineberger, W.C.; Bierbaum, V.M.,
Gas Phase Reactions of 1,3,5-Triazine: Proton Transfer, Hydride Transfer, and Anionic sigma-Adduct Formation,
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Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups,
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Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A.,
Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes,
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Fedoseenko, Yursha, et al., 1984
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya.,
Equilibrium of cyclopentanol dehydrogenation and hydrogen disproportionation in the cyclopentanol-cyclohexanone system,
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Cubberley and Mueller, 1946
Cubberley, A.H.; Mueller, M.B.,
Equilibrium studies on the dehydrogenation of primary and secondary alcohols. I. 2-Butanol, 2-octanol, cyclopentanol and benzyl alcohol,
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Determination of the proton affinities of secondary alcohols from the dissocation of proton-bound molecular trios,
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Traeger, 1985
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Heat of formation for the propanoyl cation by photoionization mass spectrometry,
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Holmes, Yuan, et al., 1977
Holmes, J.L.; Yuan, D.; Rye, R.T.B.,
Metastable ion studies VII-Loss of water from the molecular ion of cyclopentanol,
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Holmes and Lossing, 1980
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Gas-phase heats of formation of keto and enol ions of carbonyl compounds.,
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Winskowski, 1983
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Bogoslovsky, Anvaer, et al., 1978
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Rohrschneider, L.,
Eine methode zur charakterisierung von gaschromatographischen trennflüssigkeiten,
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Gas-chromatographische Charakterisierung ogranischer Verbindungen. Teil 3: Berechnung der Retentionsindices aliphatischer, alicyclischer und aromatischer Verbindungen,
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Volatile Constituents of Guava Fruits (Psidium guajava L.) and Canned Puree,
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Notes
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- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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