Interplay of Thermochemistry and Structural Chemistry, the Journal (Volume 11, 2000), and the Discipline

Structural Chemistry

Volumn 14, Issue 3, 2003, Pages 299-313

  Liebman, Joel F ^a  

^a UNIVERSITY OF MARYLAND   (United States)

Author keywords

Enthalpy of combustion; Enthalpy of formation; Enthalpy of reaction; Heat; Phase change enthalpies

Indexed keywords

ACID ANHYDRIDE; BORON; CARBON; CARBOXYLIC ACID DERIVATIVE; DIKETONE; DISULFIDE; PHOSPHORUS; SULFINIC ACID DERIVATIVE; SULFOXIDE; SULFUR;

AQUEOUS SOLUTION; CALORIMETRY; CHEMICAL INTERACTION; CHEMISTRY; COMBUSTION; CONJUGATION; ENTHALPY; MEDICAL LITERATURE; POLYMERIZATION; REVIEW; SOLVATION; STRUCTURAL CHEMISTRY; THERMOCHEMISTRY;

EID: 1642496896     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1023820031103     Document Type: Review

References (133)

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2. Indeed, the current study may be understood as the logical successor of the series of book chapters "Some Relationships between Molecular Structure and Thermochemistry" that annually appeared in the Advances in Molecular Structure Research; Hargittai, M.; Hargittai, I., Eds.; JAI Press: Greenwich, CT, 1997; Vol. 3, p. 313; 1998; Vol. 4, p. 343; 1999; Vol. 5, p. 359; 2000; Vol. 6, p. 443. (All of these studies were by S. W. Slayden and J. F. Liebman.)
3. Indeed, the current study may be understood as the logical successor of the series of book chapters "Some Relationships between Molecular Structure and Thermochemistry" that annually appeared in the Advances in Molecular Structure Research; Hargittai, M.; Hargittai, I., Eds.; JAI Press: Greenwich, CT, 1997; Vol. 3, p. 313; 1998; Vol. 4, p. 343; 1999; Vol. 5, p. 359; 2000; Vol. 6, p. 443. (All of these studies were by S. W. Slayden and J. F. Liebman.)
4. Indeed, the current study may be understood as the logical successor of the series of book chapters "Some Relationships between Molecular Structure and Thermochemistry" that annually appeared in the Advances in Molecular Structure Research; Hargittai, M.; Hargittai, I., Eds.; JAI Press: Greenwich, CT, 1997; Vol. 3, p. 313; 1998; Vol. 4, p. 343; 1999; Vol. 5, p. 359; 2000; Vol. 6, p. 443. (All of these studies were by S. W. Slayden and J. F. Liebman.)
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35. Note, these compounds are also enamines and enals, two rather ignored functional groups for the thermochemist, cf. Liebman, J. F.; Perks, H. M. In The Chemistry of Enamines; Rappoport, Z., Ed., Wiley: Chichester, UK, 1994; p. 255; Liebman, J. F.; Pollack, R. M. In The Chemistry of the Enone Functional Group; Patai, S.; Rappoport, Z., Eds,; Wiley: Chichester, UK, 1989; p. 107.
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40. This is a highly useful compendium of condensed-phase thermochemical results, many found nowhere else save the original (and often inaccessible) source of the data. Quoting directly (p. 413) "the information [on hydrazones] . . . is extremely meager, and a careful analysis of the values indicates that they do not form a homogenous [sic] series." It is to be noted that the information given by Kharasch is also extremely meager as to why he chose to ignore these hydrazone data. For completeness, we now give the original citations so that the reader can evaluate the data if s/he wishes: Landrieu, P., Compt. Rend., 1905, 141, 358; ibid. 1906, 142, 540.
41. This is a highly useful compendium of condensed-phase thermochemical results, many found nowhere else save the original (and often inaccessible) source of the data. Quoting directly (p. 413) "the information [on hydrazones] . . . is extremely meager, and a careful analysis of the values indicates that they do not form a homogenous [sic] series." It is to be noted that the information given by Kharasch is also extremely meager as to why he chose to ignore these hydrazone data. For completeness, we now give the original citations so that the reader can evaluate the data if s/he wishes: Landrieu, P., Compt. Rend., 1905, 141, 358; ibid. 1906, 142, 540.
42. We are being somewhat disingenuous here. We acknowledge that there is the condensed phase study on alkyl alkylidenehydrazones: Lebedeva, N. D.; Masalitinova, T. N.; Mon'yakova, O. N.; Oleinikova, T. P. J. Org. Chem. USSR (Engl. Transl.), 1980, 16, 226.
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44. Slayden, S. W.; Liebman, J. F. In The Chemistry of Functional Groups Supplement A3: The Chemistry of Double-Bonded Functional Groups; Patai, S. Ed., Wiley; Chichester, UK, 1997; p. 537.
45. Rogers, D. W.; McLafferty, F. J. J. Phys. Chem., 2000, 104A, 9356.
46. Bartell, L. S.; Chushak, Y. G.; Huang, J. Struct. Chem. 2000, 11, 105.
47. The 0.0 error bar in the enthalpy of vaporization corresponds to the value of 0.1 when recorded in kcal/mol as given in the archival Ref. [2].
48. Liebman, J. F. In Fluorine-Containing Molecules: Structure, Reactivity, Synthesis and Applications; Liebman, J. F.; Greenberg, A.; Dolbier, W. R., Jr., Eds; VCH: New York, 1988; p. 309.
49. ∞- " are seemingly unknown - tetrachloroethylene and tetramethylethylene do not polymerize.
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51. Recall the "diagonal" definition of strain energy, Van Vechten, D.; Liebman, J. F. Israil J. Chem. 1981, 21, 105.
52. It is to be acknowledged that there are no measurements of the enthalpy of formation of cyclooctadecane or any higher cycloalkane and so we do not know if cycloheptadecane, in fact, is the most stable cycloalkane. Cycloheptadecane has a lower recorded enthalpy of sublimation than we might have expected and so the species has anomalously little strain. Has the strain been underestimated much as that of cyclotetradecane was "historically" overestimated because its sublimation enthalpy was overestimated, cf. Chickos, J. S.; Hesse, D. G.; Panshin, S. Y.; Rogers, D. W.; Saunders, M.; Uffer, P. M.; Liebman, J. F. J. Org. Chem. 1992, 57, 1897.
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54. 6 isoelectronically "mimics" benzene. By contrast, if there are two or more, no such arguments can be given. For example, graphite is the most stable form of elemental carbon at STP despite the greater hardness and mechanical strength of diamond.
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57. This value is quite clearly twice that of the "universal methylene increment," referenced earlier in Ref. [16].
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72. 2.
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77. Admittedly, it is the greater acidity and lessened basicity of p-nitroaniline relative to its m isomer that is the more general topic of discussion that employs resonance structures of the two isomers.
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79. 2 and their hydrated derivatives, wherein the data was for crystalline salts and tetrahydrates, except for the nitrate, which the latter referred to the 1:4 aqueous solution.
80. Durig, J. R.; Shen, S.; Drew, B. R.; Zhao, W. Struct. Chem. 2000, 11, 213.
81. The enthalpy of formation of all cyclopropanes discussed in the current paper are from the thermochemical review. Liebman, J. F.; Greenberg, A. Chem. Rev. 1989, 89, 1225.
82. What we should say is that there is no consensus value we feel comfortable with because of the excessive uncertainty we are compelled to give it. There is a value for gas phase methyl vinyl ketone involving aqueous solution phase equilibrium measurements, -115 ± 11 kJ/mol, from Guthrie, J. P. Can. J. Chem. 1978, 56, 962. We can also derive a value of -107.1 by assuming the value of its liquid phase hydrogenation (131.6 kJ/mol) is the same as the corresponding, but hypothetical process in the gas phase, from Veselova, M. E.; Sul'man, E. M. Svoistva Veshchestv I Stroenie Molekul (Kalinin), 1980, p. 140.
83. What we should say is that there is no consensus value we feel comfortable with because of the excessive uncertainty we are compelled to give it. There is a value for gas phase methyl vinyl ketone involving aqueous solution phase equilibrium measurements, -115 ± 11 kJ/mol, from Guthrie, J. P. Can. J. Chem. 1978, 56, 962. We can also derive a value of -107.1 by assuming the value of its liquid phase hydrogenation (131.6 kJ/mol) is the same as the corresponding, but hypothetical process in the gas phase, from Veselova, M. E.; Sul'man, E. M. Svoistva Veshchestv I Stroenie Molekul (Kalinin), 1980, p. 140.
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97. This is most simply deduced by combining the above neutral species regularity with the observation that the ionization energy of all three fluorides are very nearly the same, cf. Berkowitz, J.; Chupka, W. A.; Guyon, P. M.; Holloway, J.; Spohr, R., Advan. Mass Spectrom. 1971, 5, 112; Berkowitz, J.; Chupka, W. A.; Guyon, P. M.; Holloway, J. H.; Spohr, R., J. Phys. Chem. 1971, 75, 1461.
98. This is most simply deduced by combining the above neutral species regularity with the observation that the ionization energy of all three fluorides are very nearly the same, cf. Berkowitz, J.; Chupka, W. A.; Guyon, P. M.; Holloway, J.; Spohr, R., Advan. Mass Spectrom. 1971, 5, 112; Berkowitz, J.; Chupka, W. A.; Guyon, P. M.; Holloway, J. H.; Spohr, R., J. Phys. Chem. 1971, 75, 1461.
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100. Taskinen, E. Struct. Chem. 2000, 11, 275.
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102. Taskinen, E. Struct. Chem. 2000, 11, 283.
103. Lactones: (a) n = 2, Schröder, D.; Goldberg, N.; Zummack, W.; Schwarz, H.; Poutsma, J. C.; Squires, R. R. Intern. J. Mass Spectry Ion Proc. 1997, 165/166, 71. (b) n = 3, Borjesson, B.; Nakase, Y.; Sunner, S. Acta Chem. Scand. 1966, 20, 803. n = 4-13, Wiberg, K. B.; Waldron, R. F. J. Amer. Chem. Soc. 1991, 113, 7697.
104. Lactones: (a) n = 2, Schröder, D.; Goldberg, N.; Zummack, W.; Schwarz, H.; Poutsma, J. C.; Squires, R. R. Intern. J. Mass Spectry Ion Proc. 1997, 165/166, 71. (b) n = 3, Borjesson, B.; Nakase, Y.; Sunner, S. Acta Chem. Scand. 1966, 20, 803. n = 4-13, Wiberg, K. B.; Waldron, R. F. J. Amer. Chem. Soc. 1991, 113, 7697.
105. Lactones: (a) n = 2, Schröder, D.; Goldberg, N.; Zummack, W.; Schwarz, H.; Poutsma, J. C.; Squires, R. R. Intern. J. Mass Spectry Ion Proc. 1997, 165/166, 71. (b) n = 3, Borjesson, B.; Nakase, Y.; Sunner, S. Acta Chem. Scand. 1966, 20, 803. (c) n = 4-13, Wiberg, K. B.; Waldron, R. F. J. Amer. Chem. Soc. 1991, 113, 7697.
106. Taskinen, E. Struct. Chem. 2000, 11, 293.
107. This result and the above reference on 1,2-dimethoxyethene are part of a general trend that species of the type X-CH=CH-Y isomers are stabilized as Z isomers as opposed to E-when X and Y have lone pair electrons, e.g., the two isomers of 1,2-diiodoethene have nearly identical enthalpies of formation, Furuyama, S.; Golden, D. M.; Benson, S. W., J. Phys. Chem. 1968, 72, 3204.
108. Rumjanek, V. M.; da Costa, J. B. N.; Echevarria, A.; Cavalcante, M. F. Struct. Chem. 2000, 11, 303.
109. We do note, however, that there are enthalpy of formation data for dihydroxymonoamino-and monohydroxydiaminotriazine (or are these in their amide tautomer): with no, 1, 2, and 3 hydroxy (or keto) groups, and 3, 2, 1, and no amino groups respectively, the archivally recommended solid phase enthalpies of formation are: 71.7 ± 0.6; -299.7 ± 2.1; -492.8 ± 4.2, and -660.4 ± 0.6 kJ/mol.
110. Pawelka, Z.; Lorenc, J.; Puszko, A. Struct. Chem. 2000, 11, 307.
111. Giricheva, N. I.; Girichev, G. V.; Girichev, A. G.; Shlykov, S. A. Struct. Chem. 2000, 11, 313.
112. Wallet, J.-C.; Molins, E.; Miravitles, C. Struct. Chem. 2000, 11, 319.
113. Are we expecting too much; the enthalpies of formation of gaseous o-, m-and p-methoxybenzoic acid are -433.8 ± 1.2, -446.1 ± 0.8, and -451.9 ± 1.4 kJ/mol, from Colomina, M.; Jiménez, P.; Roux, M. V.; Turrión, C. J. Chem. Thermodyn. 1978, 10, 661.
114. For a combined calorimetric and calculational study of the trimethoxybenzenes, see Matos, M. A. R.; Miranda, M. S.; Morais, V. M. F. J. Phys. Chem. A 2000, 104, 9260.
115. Perks, H. M.; Liebman, J. F. Struct. Chem. 2000, 11, 325.
116. Afeefy, H. Y.; Liebman, J. F. In Computational Thermochemistry: Prediction and Estimation of Molecular Thermodynamics, Frurip, D. J.; Irikura, K. K., Eds.; ACS Symposium Series 677: Washington DC, 1998, p. 94.
117. For a study (experimental hydrogenation enthalpies and quantum chemical) of the strain energies of [5] and [6]metacyclophane, see van Eis, M. J.; Wijsman, G. W.; de Wolf, W. H.; Bickelhaupt, F.; Rogers, D. W.; Kooijman, H.; Spek. A. Chem. Eur. J. 2000, 6, 1537.
118. Alkorta, I.; Elguero, J. Struct. Chem. 2000, 11, 335.
119. (a) Liebman, J. F. In The Chemistry of the Sulphonic Acids, Esters and Their Derivatives, Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, UK, 1991, p. 283.
120. (b) Ribeiro da Silva, M. A. V.; Ferrao, M. L. C. C. H.; Lopes, A. J. M. J. Chem. Thermodyn. 1993, 25, 229.
121. Recalling the nearly constant enthalpy of formation difference of corresponding vinyl and phenyl derivatives, (cf. Ref. [23]), we now acknowledge that this relation is much less valid for charged species. Hunter, E. P.; Lias, S. G.; Rooney, C. M.; Winstead, J. L.; Liebman, J. F. Intern. J. Mass Spectry Ion Proc., 1998, 179/180, 261.
122. Fantola-Lazzarini, A.; Lazzarini, E. Struct. Chem. 2000, 11, 341.
123. Facibeni-Giribone, A.; Fantola-Lazzarini, A. L.; Lazzarini, E. Struct. Chem. 2000, 11, 347.
124. Pavlović, G.; Lapić, J.; Rapić, V. Struct. Chem. 2000, 11, 355.
125. Galić, N.; Matković-Čalogović, D.; Cimerman, Z. Struct. Chem. 2000, 11, 361.
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130. Liebman, J. F.; Crawford, K. S. K.; Slayden, S. W. In The Chemistry of Functional Groups Supplement S: The Chemistry of Sulphur-Containing Functional Groups, Patai, S.; Rappoport, Z. Eds.; Wiley: Chichester, UK, 1993; p. 197.
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133. For an application to some tetraatomic species with dicoordinate boron and phosphorus, see Liebman, J. F.; Černušák, I.; Milková, A. Intern. J. Quantum Chem. 2001, 84, 140.