Infrared intensities. Use of the CH-stretching band intensity as a tool for evaluating the acidity of hydrogen atoms in hydrocarbons

Journal of Molecular Structure

Volumn 521, Issue 1-3, 2000, Pages 1-18

  Gussoni, M ^a   Castiglioni, C ^b  

^a CNR   (Italy)

^b POLITECNICO DI MILANO   (Italy)

Author keywords

Acidity of hydrogen; CH stretching band intensity; Infrared intensities

Indexed keywords

HYDROCARBON; HYDROGEN;

ACIDITY; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; ELECTRICITY; HYBRIDIZATION; INFRARED RADIATION; STRUCTURE ANALYSIS;

EID: 0034724243     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-2860(99)00421-4     Document Type: Article

References (101)

1. Overend J. Quantitative intensity studies and dipole moment derivatives. Davies M. Infrared Spectroscopy and Molecular Structure. 1963;345 Elsevier, Amsterdam.
2. Crawford B. Vibrational intensities II. The use of isotopes. J. Chem. Phys. 20:1952;977.
3. Gussoni M., Abbate S., Zerbi G. Prediction of infrared and Raman intensities by parametric methods. Barnes A.J., Orville-Thomas W.J. Vibrational Spectroscopy: Modern Trends. 1977;205-222 Elsevier, Amsterdam.
4. Gussoni M. Infrared and Raman intensities from electrooptical parameters. Clark R.J.H., Hester R.E. Advances in Infrared and Raman Spectroscopy. 6:1979;Heyden, London.
5. Gussoni M., Abbate S. Infrared absorption intensities. Transferability of electrooptical parameters. J. Chem. Phys. 65:1976;3439.
6. Abbate S., Gussoni M. Infrared absorption intensities. Symmetry considerations on the electrooptical parameters. J. Mol. Spectrosc. 66:1977;1.
7. Abbate S., Gussoni M. On the sign of the dipole moment derivatives in methyl halides. Chem. Phys. 40:1979;385.
8. Gussoni M., Jona P., Zerbi G. Atomic charges and charge flows from infrared intensities: CH bonds. J. Chem. Phys. 78:1983;6802.
9. Castiglioni C., Gussoni M., Zerbi G. A simple way of obtaining information on charge distribution in molecules directly from infrared spectra: the case of CH bonds. J. Mol. Struct. 198:1989;475.
10. Mills I.M. Force constants calculations for small molecules. Davies M. Infrared Spectroscopy and Molecular Structure. 1963;166 Elsevier, Amsterdam.
11. Gussoni M. Role of the vibrational intensities in the determination of the molecular structure and charge distribution. J. Mol. Struct. 113:1984;323.
12. Gussoni M. Infrared intensities: a new tool in chemistry. J. Mol. Struct. 141:1986;63.
13. 3 chloride, bromide and iodide. J. Chem. Phys. 27:1957;445.
14. Nyquist I.M., Mills I.M., Person W.B., Crawford B. Vibrational intensities. VII. Ethane and ethane-d6. J. Chem. Phys. 26:1957;552.
15. Hornig D.F., McKean D.C. Bond moments and molecular structure. J. Phys. Chem. 59:1955;1133.
16. Mills I.M. Infrared intensities. Ann. Rep. Prog. Chem. (Chem. Soc. London). LV:1958;55.
17. Person W.B., Newton J.H. Dipole moment derivatives and infrared intensities. I. Polar tensor. J. Chem. Phys. 61:1974;1040.
18. Biarge J.F., Herranz J., Morcillo J. On the interpretation of infrared intensities in gases. An. Fiz. y Quim. 157:1961;81.
19. 3. J. Mol. Struct. 3:1969;77.
20. 2. Spectrochim. Acta. 22:1966;1969.
21. King W.T., Mast G.B., Blanchette P.B. Infrared intensity sum rule and effective changes. J. Chem. Phys. 53:1972;4440.
22. Bruns R.E., Brown R.E. Mean dipole moment derivatives, atomic anisotropies and effective charges of diatomic hydrides. J. Chem. Phys. 68:1978;880.
23. Volkenshtein M.V., Elyashevich M.A., Stepanov B. The theory of vibrational spectra of polyatomic molecules. I. The problem of the theory. Zh. Eksp. Tcor. Fiz. 15:1945;35.
24. Gribov L.A. Intensity Theory for Infrared Spectra of Polyatomic Molecules. 1964;Consultant's Bureau, New York.
25. Sverdlov L.M., Kovner M.A., Krainov E.P. Vibrational Spectra of Polyatomic Molecules. 1972;Wiley, New York.
26. Abbate S., Gussoni M., Masetti G., Zerbi G. Infrared and Raman intensities of polyethylene and perdeuteropolyethylene by electrooptical parameters. Single chain. J. Chem. Phys. 67:1977;1519.
27. Person W.B., Zerbi G. Vibrational Intensities in Infrared and Raman Spectroscopy. 1983;Elsevier, Amsterdam.
28. van Straten A.J., Smit W.M. Bond charge parameters from integrated infrared intensities. J. Mol. Struct. 62:1976;297.
29. vanStraten A.J., Smit W.M. Relationships between the intensity formulations. Application to ammonia and phosphine. J. Mol. Spectrosc. 65:1977;202.
30. Decius J.C. An effective atomic charge model for infrared intensities. J. Mol. Spectrosc. 57:1975;348.
31. Gussoni M., Castiglioni C., Zerbi G. Physical meaning of electrooptical parameters derived from infrared intensities. J. Phys. Chem. 88:1984;600.
32. Castiglioni C., Gussoni M., Zerbi G. Characteristic infrared intensities of CH bonds. J. Mol. Struct. 141:1986;341.
33. McKean D.C. Individual CH bond strengths in simple organic compounds: effects of conformation and substitution. Chem. Soc. Rev. 7:1978;399.
34. Lide D.R. Handbook of Chemistry and Physics. 1990;CRC Press, Boston. also 1991.
35. Herzberg G. Molecular Spectra and Molecular Structure. II. Infrared and Raman Spectra of Polyatomic Molecules. 1960;van Nostrand, New York.
36. Tanabe K., Saeki S. Calculation of infrared band intensities of various chlorinated ethanes. Bull. Chem. Soc. Jpn. 45:1972;32.
37. Jona P., Gussoni M., Zerbi G. Interpretation of infrared intensities of acetylene, propyne and 2-butyne. A common set of EOP. J. Phys. Chem. 85:1981;2210.
38. Bellamy L.J., Mayo D.W. Infrared frequency effects of lone pairs interactions with antibonding orbitals of adjacent atoms. J. Phys. Chem. 80:1976;1237.
39. M. Tommasini, Origini moleculari della risposta ottica non lineare in sistemi organici a basso gap: uno studio basato sui metodi della meccanica quantistica. PhD thesis, Politecnico di Milano, 1998.
40. Kindness A., McKean D.C., Stewart D. Infrared intensities of CH stretching bands in partially deuterated compounds, and effects of conformation and substitution. J. Mol. Struct. 224:1990;1990.
41. Kondo S., Saeki S. Infrared absorption intensities of ethane and propane. Spectrochim. Acta A. 29:1973;735.
42. Kondo S., Nakanaga T., Saeki S. Study on the infrared band intensities of cyclopropane. Spectrochim. Acta A. 35:1979;181.
43. Snyder R.G., Schactschneider J.H. Vibrational analysis of n-paraffins. I. Assignments of infrared bands in the spectra of C-3H8 though C-19H40. Spectrochim. Acta. 19:1963;85.
44. Schactschneider J.H., Snyder R.G. Vibrational analysis of n-paraffins. II. Normal coordinates calculations. Spectrochim. Acta. 19:1963;117.
45. Synder R.G., Zerbi G. Vibrational analysis of ten simple aliphatic ethers: spectra, assignments, valence force field and molecular conformation. Spectrochim. Acta A. 23:1967;391.
46. McKean D.C., Duncan J.L., Batt L. CH stretching frequencies, bond lengths and dissociation energies. Spectrochim. Acta A. 29:1973;1037.
47. McKean D.C. Interpreting the CH stretching region, through infrared partial deuteration studies. Croatica Chem. Acta. 61:1988;447.
48. E. Villa, Il ruolo della sostituzione alcossidica nella struttura e nelle propriet elettroniche di materiali eteraromatici: studio spettroscopico. PhD thesis, Universita' di Milano, 1994.
49. Mills I.M., Thompson H.W. Intensities of IR bands. Bond polar properties in dimethylacetylene. Proc. R. Soc. A. 228:1955;287.
50. Kondo S., Koga Y. Infrared absorption of methylacetylene. J. Chem. Phys. 69:1978;4022.
51. Rogers J.D., Rub B., Goldmann S., Person W.B. Measurement of infrared intensities for fundamental vibrations of gaseous acetone. J. Phys. Chem. 85:1981;3727.
52. Vaklhueva V.I., Finkel A.G., Sverdlov L.M., Andreeva A.I. Theoretical and experimental investigation on absolute band intensities in the IR spectra of polyatomic molecules. II. Acetaldehyde. Opt. Spectrosc. XXV:1968;234.
53. Koga Y., Kondo S., Saeki S., Person W.B. Infrared intensities of acetonitrile. J. Phys. Chem. 88:1984;3152.
54. Khlifi M., Raulin F. Infrared intensities and frequencies of 2-butynenitrile. Application to the atmosphere of Titan. Spectrochim. Acta A. 47:1991;171.
55. 3. J. Mol. Struct. 393:1997;73.
56. Nakanaga T. Infrared band intensities of ethylenoxide. J. Chem. Phys. 74:1981;5384.
57. Caillod J., Saur O., Lavalley J.C. Infrared spectroscopic study of the carbon-hydrogen vibrations of cyclic compounds 1,4-dioxane, 1,4-di-thione, 1,4-oxathione and cyclohexane. Spectrochim. Acta A. 36:1980;185.
58. Snyder R.G., Aljibury A.L., Strauss H.L., Casal H.L., Gough K.M., Murphy W.F. Isolated CH stretching vibrations of n-alkanes: assignment and relation to structure. J. Chem. Phys. 81:1984;5352.
59. Bode J.H.G., Smit W.M.A. Absolute infrared intensities of methane. Dipole moment derivatives and bond charge parameters. J. Phys. Chem. 84:1980;198.
60. Tanabe K., Saeki S. Calculation of infrared band intensities of various chlorinated methanes. Spectrochim. Acta A. 26:1970;1469.
61. Russell J.W., Needham C.D., Overend J. Vibrational intensities. XV. Error treatment and its application to the methyl halides. J. Chem. Phys. 45:1966;3383.
62. vanStraten A.J., Smit W.M.A. Absolute infrared intensities of methyl bromide and all deuterated derivatives. J. Chem. Phys. 67:1977;970.
63. Mizuno M., Saeki S. Infrared absorption intensities of methylene fluoride. Spectrochim. Acta A. 32:1976;1077.
64. Saeki S., Tanabe K. Calculation of infrared band intensities of methylene chloride in vapour and liquid phases. Spectrochim. Acta A. 25:1969;1325.
65. Newton J.H., Levine R.A., Person W.B. Dipole moment derivatives and infrared intensities. III. Transferable polar tensors for fluorinated methanes. J. Chem. Phys. 67:1977;3282.
66. Diem M., Nafie A., Burrow B.F. Analysis of the gas phase IR spectrum of bromochloromethane. J. Mol. Spectrosc. 71:1978;446.
67. Bertie J.E., Zhang S.L. Infrared intensities of liquids: XXI. Integrated absolute intensities of methanol and deuteroderivatives. J. Mol. Struct. 413:1997;333.
68. McKean D.C., Kindness A., Wilkie N., Murphy W.F. Experimental and ab initio infrared intensities in dimethylether: atomic polar tensors and atomic charges. Spectrochim. Acta A. 52:1996;445.
69. Murphy W.F., McKean D.C., Coats A.M., Kidness A., Wilki N. Raman and infrared intensities in trimethylamine species, polarizability and dipole derivatives and effective charges. J. Raman Spectrosc. 26:1995;763.
70. Stolov A.A., Kohan N.V., Remizov A.B. Infrared band intensities of 1,2-dibromoethane in solutions: electrostatic effect and influence of hydrogen bonding on the conformational equilibrium. Vibrational Spectrosc. 14:1997;35.
71. Golike R.C., Mills I.M., Person W.B., Crawford B. Intensities of ethylene and its deuteroisotopes. J. Chem. Phys. 25:1956;1267.
72. Wiberg K.B., Rosenberg R.E. Butadiene-1. A normal coordinate analysis and IR intensities. Structure of the second rotamer. J. Am. Chem. Soc. 112:1990;1509.
73. Koga I., Kondo S., Nakanaga T., Saeki S. Infrared absorption intensities of allene. J. Chem. Phys. 71:1979;2404.
74. Jalsovski G. Analysis of IR intensities in formaldehyde. J. Mol. Struct. 19:1973;783.
75. Mizuno M., Saeki S. Infrared absorption intensities of formyl fluoride. Spectrochim. Acta A. 34:1978;407.
76. Notholt J., Cappellani F., Roesdahl H., Restelli G. Absolute infrared intensity and air broadening coefficients for spectroscopic measurement of formic acid in air. Spectrochim. Acta A. 47:1991;477.
77. Olichmann H.J., Bougeard D., Schrader B. Coupled calculations of vibrational frequencies and intensities. Part V. Infrared and Raman spectra of glyoxal and acrolein. J. Mol. Struct. 77:1981;149.
78. Kagel R.O., Powell D.W., Overend J., Ramos M.N., Bassi A.B.M.S., Bruns R.E. Infrared gas-phase intensity measurement, polar tensors, effective charges of cis-difluoro- and its deuterated modifications. J. Chem. Phys. 78:1983;7029.
79. Kagel K.O., Powell D.L., Overend J. Vibrational intensities. 24. Data processing system for IR gas phase intensity measurements. Appl. Optics. 7:1968;2075.
80. Kagel R.O., Powell D.L., Overend J., Ramos M.N., Bassi A.B.M.S., Bruns R.E. Infrared gas-phase intensity measurement, polar tensors, effective charges of viniliden fluoride and its deuterated modifications. J. Chem. Phys. 77:1982;1099.
81. Hopper M.J., Overend J., Ramos M.N., Bassi A.B.M., Bruns R.E. Infrared gas-phase intensity measurement. Polar tensors and effective charges of cis-dichloroethylene-d0 and d2. J. Chem. Phys. 79:1983;19.
82. Kagel R.O., Powell D.L., Hopper M.J., Overend J., Ramos M.N., Bassi A.B.M.S., Bruns R.E. Infrared gas-phase intensity measurement, polar tensors, effective charges of trans-difluoro- and trans-dichloro-ethylene. J. Phys. Chem. 88:1984;521.
83. Spedding H., Whiffen D.H. Intensities in the infrared spectrum of benzene. Proc. R. Soc. A. 238:1956;245.
84. Gussoni M., Castiglioni C., Miragoli M., Lugli G., Zerbi G. Derivation of charge distribution from infrared intensities; the case of polyacetylene. Spectrochim. Acta A. 41:1985;37.
85. Kim K., King W.T. Integrated infrared intensities in HCCH, DCCD, HCCD. J. Mol. Struct. 57:1979;201.
86. Khlifi M., Raulin F., Azic E., Graner G. Absolute intensity of the IR bands of propynenitrile. J. Mol. Spectrosc. 143:1990;209.
87. Koops T., Visser T., Smit W.M.A. The harmonic force field and absolute infrared intensities of diacetylene. J. Mol. Struct. 125:1984;179.
88. Hyde G.E., Hornig D.F. The measurement of bond moments and derivatives of HCN and DCN from infrared intensities. J. Chem. Phys. 20:1952;647.
89. Da Costa N.B., Aquino A.J.A., Ramos M.N., Castiglioni C., Zerbi G. The trans effect of lone pairs in individual X-H bonds (X=C,N). An ab initio study. Adv. Chem. Phys. 75:1989;37.
90. Hernandez V., Castiglioni C., Zerbi G. Hyperconjugation from IR intensities. The case of methyl acetate and of its selectively deuterated derivatives. J. Mol. Struct. 324:1994;181.
91. Gussoni M., Castiglioni C., Zerbi G. Charge distribution from infrared intensities: charges on hydrogen atoms and hydrogen bond. J. Chem. Phys. 80:1984;1377.
92. Castiglioni C., Gussoni M., Zerbi G. Stabilization energy of weak hydrogen bonded molecular complexes. Comparison of simple models. J. Chem. Phys. 80:1984;3916.
93. Rui M., Ramos M.N., Castiglioni C., Gussoni M., Zerbi G. Charge distribution in halogenated hydrocarbons and intermolecular interactions. A way for determining compatibility in polymer blends. Mol. Cryst. Liq. Cryst. 187:1990;275.
94. Coleman M.M., Painter P.C. Polymer blends. Appl. Spectrosc. Rev. 20:1984;255.
95. Varnell D.F., Moskala E.J., Painter P.C., Coleman M.M. Application of FTIR spectroscopy to the elucidation of specific interactions in miscible polyester-polyvinylchloride blends. Polym. Engng Sci. 23:1983;658.
96. Stanghellini P.L., Rossetti R. Infrared frequencies and intensities of the vibrational modes of alkynes coordinated on metal carbonyl clusters. Inorg. Chem. 29:1990;2047.
97. Diana E., Rossetti R., Stanghellini P.L. Mater. Chem. Phys. 29:1991;333.
98. y fragments bonded to metal complexes. Relationship with structure, bonding and reactivity. Spectrochim. Acta A. 49:1993;1247.
99. R. Radaelli, Delocalizzaione di elettroni π intra- e inter- unita' monomeriche, in monomeri a geometria costretta e nei polimeri. Spettri elettronici e vibrazionali. PhD thesis, Universita' di Milano, 1991.
100. 10. Acta Cryst. C. 40:1984;1210.
101. Cosmo R., Hambley T.W., Stenell S. Skeletal deformation in 4,5-disubstituted 9,10-dihydrophenanthrenes and 4,5-disubstituted phenanthrenes. J. Org. Chem. 52:1987;3119.