Elementary peptide motifs in the gas phase: FTIR aggregation study of formamide, acetamide, N-methylformamide, and N-methylacetamide

Journal of Physical Chemistry A

Volumn 112, Issue 33, 2008, Pages 7530-7542

  Albrecht, Merwe ^a   Rice, Corey A ^a,b   Suhm, Martin A ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

FORM AMIDES; GAS-PHASE;

AMINES; CHLORINE COMPOUNDS; DIMERS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GAS DYNAMICS; HYDROCARBONS; OLIGOMERS; QUENCHING;

AMIDES;

ACETAMIDE; ACETAMIDE DERIVATIVE; FORMAMIDE DERIVATIVE; N METHYLACETAMIDE; N METHYLFORMAMIDE; N-METHYLACETAMIDE; PEPTIDE;

ARTICLE; CHEMISTRY; GAS; INFRARED SPECTROSCOPY; PROTEIN MOTIF;

ACETAMIDES; AMINO ACID MOTIFS; FORMAMIDES; GASES; PEPTIDES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 51049094002     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp8039912     Document Type: Article

References (97)

1. Guo, H.; Karplus, M. Ab Initio Studies of Hydrogen Bonding of N-Methylacetamide: Structure, Cooperativity, and Internal Rotational Barriers. J. Phys. Chem. 1992, 96, 7273-7287.
2. Kobko, N.; Dannenberg, J. J. Cooperativity in Amide Hydrogen Bonding Chains. A Comparison between Vibrational Coupling through Hydrogen Bonds and Covalent Bonds. Implications for Peptide Vibrational Spectra. J. Phys. Chem. A 2003, 107, 6688-6697.
3. Tan, H.; Qu, W.; Chen, G.; Liu, R. The Role of Charge Transfer in the Hydrogen Bond Cooperative Effect of cis-N-Methylformamide Oligomers. J. Phys. Chem. A 2005, 109, 6303-6308.
4. Frey, J. A.; Leutwyler, S. An ab Initio Study of Hydrogen Bonded Formamide Dimers. J. Phys. Chem. A 2006, 110, 12512-12518.
5. Surewicz, W. K.; Mantsch, H. H.; Chapman, D. Determination of Protein Secondary Structure by Fourier Transform Infrared Spectroscopy: A Critical Assessment. Biochemistry 1993, 32 (2), 389-394.
6. Torii, H.; Tatsumi, T.; Kanazawa, T.; Tasumi, M. Effects of Intermolecular Hydrogen-Bonding Interactions on the Amide I Mode of N-Methylacetamide: Matrix-Isolation Infrared Studies and ab Initio Molecular Orbital Calculations. J. Phys. Chem. B 1998, 102, 309-314.
7. Chalupsky, J.; Vondrášek, J.; Špirko, V. Quasiplanarity of the Peptide Bond. J. Phys. Chem. A 2008, 112, 693-699.
8. Dauster, I.; Rice, C. A.; Zielke, P.; Suhm, M. A. N-H⋯π interactions in pyrroles: systematic trends from the vibrational spectroscopy of clusters. Phys. Chem. Chem. Phys. 2008, 10, 2827-2835.
9. Rice, C. A.; Borho, N.; Suhm, M. A. Dimerization of Pyrazole in Slit Jet Expansions. Z. Phys. Chem. 2005, 279, 379-388
10. Wassermann, T. N.; Rice, C. A.; Suhm, M. A.; Luckhaus, D. Hydrogen bonding lights up overtones in pyrazoles. J. Chem. Phys. 2007, 127, 234309.
11. Frey, J. A.; Müller, A.; Losada, M.; Leutwyler, S. Isomers of the Uracil Dimer: An ab Initio Benchmark Study. J. Phys. Chem. B 2007, 111, 3534-3542.
12. Gerhards, M.; Unterberg, C.; Gerlach, A.; Jansen, A. β-Sheet model systems in the gas phase: Structures and vibrations of Ac-Phe-NHMe and its dimer (Ac-Phe-NHMe)2. Phys. Chem. Chem. Phys. 2004, 6, 2682-2690.
13. Jones, R. L. Infrared Evidence for the Occurrence of Restricted Rotation in N-Methylformamide. J. Mol. Spectrosc. 1958, 2, 581-586.
14. Kutzelnigg, W.; Mecke, R. Spektroskopische Untersuchungen an organischen Ionen. 5. Die Struktur der Salze des Acetamids. Spectrochim. Acta 1962, 18, 549-560.
15. Florián, J.; Johnson, B. G. Structure, Energetics, and Force Fields of the Cyclic Formamide Dimer: MP2, Hartree-Fock, and Density Functional Study. J. Phys. Chem. 1995, 99, 5899-5908.
16. Herrebout, W. A.; Clou, K.; Desseyn, H. O. Vibrational Spectroscopy of N-Methylacetamide Revisited. J. Phys. Chem. A 2001, 105, 4865-4881.
17. Kubelka, J.; Keiderling, T. A. Ab Initio Calculation of Amide Carbonyl Stretch Vibrational Frequencies in Solution with Modified Basis Sets. 1. N-Methyl Acetamide. J. Phys. Chem. A 2001, 105, 10922-10928.
18. Gómez Marigliano, A. C.; Varetti, E. L. Self-Association of Formamide in Carbon Tetrachloride Solutions: An Experimental and Quantum Chemistry Vibrational and Thermodynamic Study. J. Phys. Chem. A 2002, 106, 1100-1106.
19. Cabaleiro-Lago, E. M.; Rodríguez Otero, J. Ab Initio and density functional theory study of the interaction in formamide and thioformamide dimers and trimers. J. Chem. Phys. 2002, 117(4), 1621-1632.
20. Watson, T. M.; Hirst, J. D. Density Functional Theory Vibrational Frequencies of Amides and Amide Dimers. J. Phys. Chem. A 2002, 106, 7858-7867.
21. Papamokos, G. V.; Demetropoulos, I. N. Vibrational Frequencies of Amides and Amide Dimers: The Assessment of PW91XC Functional. J. Phys. Chem. A 2004, 108, 7291-7300.
22. Köddermann, T.; Ludwig, R. N-Methylacetamide/water clusters in a hydrophobic solvent. Phys. Chem. Chem. Phys. 2004, 6, 1867-1873.
23. Lucas, B.; Grégoire, G.; Lecomte, F.; Schermann, J.-P.; Desfrançois, C. Infrared spectroscopy of mass-selected neutral molecular systems without chromophore: the formamide monomer and dimer. Mol. Phys. 2005, 103, 1497-1503.
24. Lu, J.-f.; Zhou, Z.-y.; Wu, Q.-y.; Zhao, G. Density functional theory study of the hydrogen bonding interaction in formamide dimer. J. Mol. Struct. (Theochem) 2005, 724, 107-114.
25. Shin, S.; Kurawaki, A.; Hamada, Y.; Shinya, K.; Ohno, K.; Tonara, A.; Sato, M. Conformational behavior of N-methylformamide in the gas, matrix, and solution states as revealed by IR and NMR spectroscopic measurements and by theoretical calculations. J. Mol. Struct. 2006, 791, 30-40.
26. Mardyukov, A.; Sanchez-Garcia, E.; Rodziewicz, P.; Doltsinis, N. L.; Sander, W. Formamide Dimers: A Computational and Matrix Isolation Study. J. Phys. Chem. A 2007, 111, 10552-10561.
27. Colominas, C.; Luque, F. J.; Orozco, M. Dimerization of formamide in gas phase and solution. An Ab Initio MC-MST Study. J. Phys. Chem. A 1999, 103, 6200-6208.
28. Gaigeot, M. P.; Vuilleumier, R.; Sprik, M.; Borgis, D. Infrared Spectroscopy of N-Methylacetamide Revisited by ab Initio Molecular Dynamics Simulation. J. Chem. Theory Comput. 2005, 1, 772-789.
29. Gregurick, S. K.; Chaban, G. M.; Gerber, R. B. Ab Initio and Improved Empirical Potentials for the Calculation of the Anharmonic Vibrational States and Intramolecular Mode Coupling of N-Methylacetamide. J. Phys. Chem. A 2002, 106, 8696-8707.
30. Bounouar, M.; Scheurer, C. Reducing the vibrational coupling network in N-methylacetamide as a model for ab initio infrared spectra computations of peptides. Chem. Phys. 2006, 323, 87-101.
31. Kaledin, A. L.; Bowman, J. M. Full Dimensional Quantum Calculations of Vibrational Energies of N-Methyl Acetamide. J. Phys. Chem. A 2007, 111, 5593-5598.
32. Robertson, E. G.; Hockridge, M. R.; Jelfs, P. D.; Simons, J. P. IR-UV ion-depletion and fluorescence spectroscopy of 2-phenylacetamide clusters: hydration of a primary amide. Phys. Chem. Chem. Phys. 2001, 3, 786-795.
33. Shubert, V. A.; Baquero, E. E.; Clarkson, J. R.; James, W. H., III; Turk, J. A.; Hare, A. A.; Worrel, K.; Lipton, M. A.; Schofield, D. P.; Jordan, K. D.; Zwier, T. S. Entropy-driven population distributions in a prototypical molecule with two flexible side chains: O-(2-acetamidoethyl)-N-acetyltyramine. J. Chem. Phys. 2007, 127, 234315.
34. Borba, A.; Gómez-Zavaglia, A.; Fausto, R. Molecular Structure, Vibrational Spectra, Quantum Chemical Calculations and Photochemistry of Picolinamide and Isonicotinamide Isolated in Cryogenic Inert Matrixes and in the Neat Low-Temperature Solid Phases. J. Phys. Chem. A 2008, 112, 45-57.
35. Pohl, G.; Perczel, A.; Vass, E.; Magyarfalvi, G.; Tarczay, G. A matrix isolation study on Ac-Gly-NHMe and Ac-L-Ala-NHMe, the simplest chiral and achiral building blocks of peptides and proteins. Phys. Chem. Chem. Phys. 2007, 9, 4698-4708.
36. Demaison, J.; Császár, A. G.; Kleiner, I.; Møllendal, H. Equilibrium vs ground-state planarity of the CONH linkage. J. Phys. Chem. A 2007, 111, 2574-2586.
37. McNaughton, D.; Evans, C. J.; Lane, S.; Nielsen, C. J. The High-Resolution FTIR Far-Infrared Spectrum of Formamide. J. Mol. Spectrosc. 1999, 193, 104-117.
38. Jurečka, P.; Sponer, J.; Černý, J.; Hobza, P. Benchmark database of accurate (MP2 and CCSD(T) complete basis set limit) interaction energies of small model complexes, DNA base pairs, and amino acid pairs. Phys. Chem. Chem. Phys. 2006, 8, 1985-1993.
39. Schwabe, T.; Grimme, S. Double-hybrid density functionals with long- range dispersion corrections: higher accuracy and extended applicability. Phys. Chem. Chem. Phys. 2007, 9, 3397-3406.
40. 3 barrier of cis N-methylformamide: A-E doubling from the free jet rotational spectrum. J. Mol. Spectrosc. 2002, 672, 305-307.
41. Fantoni, A. C.; Caminati, W. Rotational spectrum and ab initio calculations of N-methylformamide. J. Chem. Soc., Faraday Trans. 1996, 92 (3), 343-346.
42. Wiberg, K. B.; Rush, D. J. Methyl Rotational Barriers in Amides and Thioamides. J. Org. Chem. 2002, 67, 826-830.
43. Avalos, M.; Babiano, R.; Barneto, J. L.; Bravo, J. L.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Can we predict the conformational preference of amides? J. Org. Chem. 2001, 66, 7275-7282.
44. Whitfield, T. W.; Martyna, G. J.; Allison, S.; Bates, S. P.; Vass, H.; Crain, J. Structure and Hydrogen Bonding in Neat N-Methylacetamide: Classical Molecular Dynamics and Raman Spectroscopy Studies of a Liquid of Peptidic Fragments. J. Phys. Chem. B 2006, 770, 3624-3637.
45. Nesbitt, D. J. High-resolution, direct infrared laser absorption spectroscopy in slit supersonic jets: intermolecular forces and unimolecular vibrational dynamics in clusters. Annu. Rev. Phys. Chem. 1994, 45, 367-399.
46. Liu, K.; Fellers, R. S.; Viant, M. R.; McLaughlin, R. P.; Brown, M. G.; Saykally, R. J. A long path length pulsed slit valve appropriate for high temperature operation: Infrared spectroscopy of jet-cooled large water clusters and nucleotide bases. Rev. Sci. Instrum. 1996, 67, 410-416.
47. Borho, N.; Suhm, M. A.; Le Barbu-Debus, K.; Zehnacker, A. Intra- vs. Intermolecular Hydrogen Bonding: Dimers of alpha-Hydroxyesters with Methanol. Phys. Chem. Chem. Phys. 2006, 8, 4449-4460.
48. In a continuation of our culinary acronyms for different nozzle and cluster spectrometer designs, we denote this nozzle as poppet controlled resistively heated nozzle (popcorn) having in mind the liquid-soaked molecular sieve or crystal grains which deliver the required vapor pressure upon heating.
49. Cézard, C.; Rice, C. A.; Suhm, M. A. OH-Stretching Redshifts in Bulky Hydrogen-Bonded Alcohols: Jet Spectroscopy and Modeling. J. Phys. Chem. A 2006, 110, 9839-9848.
50. Fárník, M.; Weimann, M.; Suhm, M. A. Acidic protons before takeoff: A comparative jet Fourier transform infrared study of small HCl- and HBr-solvent complexes. J. Chem. Phys. 2003, 118, 10120-10136.
51. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revisions B. 04 and C. 02; Gaussian Inc.: Pittsburgh, PA, 2003.
52. Wong, M. W.; Wiberg, K. B. Structure of Acetamide: Planar or Nonplanar. J. Phys. Chem. 1992, 96, 668-671.
53. Samdal, S. Acetamide, a challenge to theory and experiment? On the molecular structure, conformation, potential to internal rotation of the methyl group and force fields of free acetamide as studied by quantum chemical calculations. J. Mol. Struct. 1998, 440, 165-174.
54. Jeffrey, G. A.; Ruble, J. R.; McMullan, R. K.; DeFrees, D. J.; Binkley, J. S.; Pople, J. A. Neutron Diffraction at 23 K and ab initio Molecular-Orbital Studies of the Molecular Structure of Acetamide. Acta Crystallogr, Sect. B 1980, 36, 2292-2299.
55. Brummel, C. L.; Shen, M.; Hewett, K. B.; Philips, L. A. High-resolution infrared spectroscopy of formamide and deuterated formamide in a molecular beam. J. Opt. Soc. Am. B. 1994, 77 (1), 176-183.
56. Zhao, Y.; Truhlar, D. G. Infinite-Basis Calculations of Binding Energies for the Hydrogen Bonded and Stacked Tetramers of Formic Acid and Formamide and Their Use for Validation of Hybrid DFT and ab Initio Methods. J. Phys. Chem. A 2005, 709 (30), 6624-6627.
57. Ladell, J.; Post, B. The Crystal Structure of Formamide. Acta Crystallogr. 1954, 7, 559-564.
58. Iogansen, A. V.; Kurkchi, G. A.; Dementjeva, L. A. Infrared spectra in the VNH region and structures of associated species of acetamide. J. Mol. Struct. 1976, 35, 101-114.
59. Räsänen, M. A Matrix Infrared Study of Monomeric Formamide. J. Mol. Struct. 1983, 101, 275-286.
60. Räsänen, M. A Matrix Infrared Study of Association of Formamide. J. Mol. Struct. 1983, 702, 235-242.
61. 2 "Inversion" Vibration for Formamide in the Vapor Phase and in an Argon Matrix. J. Phys. Chem. 1971, 75 (3), 405-410.
62. Larsen, R. W.; Zielke, P.; Suhm, M. A. Hydrogen-bonded OH stretching modes of methanol clusters: A combined IR and Raman isotopomer study. J. Chem. Phys. 2007, 126, 194307.
63. Zielke, P.; Suhm, M. A. Concerted proton motion in hydrogen-bonded trimers: A spontaneous Raman scattering perspective. Phys. Chem. Chem. Phys. 2006, 8, 2826-2830.
64. Rice, C. A.; Dauster, I.; Suhm, M. A. Infrared spectroscopy of pyrrole-2-carboxaldehyde and its dimer: A planar β-sheet peptide model? J. Chem. Phys. 2007, 126, 134313.
65. Emmeluth, C.; Suhm, M. A.; Luckhaus, D. A monomers-in-dimers model for carboxylic acid dimers. J. Chem. Phys. 2003, 118, 2242-2255.
66. Duvernay, F.; Chatron-Michaud, P.; Borget, F.; Birney, D. M.; Chiavassa, T. Photochemical dehydration of acetamide in a cryogenic matrix. Phys. Chem. Chem. Phys. 2007, 9, 1099-1106.
67. Knudsen, R.; Sala, O.; Hase, Y. A low temperature matrix isolation infrared study of acetamides. I. Acetamide and some deuterated derivatives. J. Mol. Struct. 1994, 327, 187-195.
68. 4. Spectrochim. Acta, Part A 1972, 28, 165-175.
69. Emmeluth, C.; Suhm, M. A. A chemical approach towards the spectroscopy of carboxylic acid dimer isomerism. Phys. Chem. Chem. Phys. 2003, 5, 3094-3099.
70. Davies, M.; Hallam, H. E., III. Molecular interaction and infrared absorption spectra. Part III. Acetamide Trans. Faraday Soc. 1951, 47 (11), 1170-1181.
71. Denne, W. A.; Small, R. W. H. A refinement of the structure of rhombohedral acetamide. Acta Crystallogr., Sect. B 1971, 27, 1094-1098.
72. Senti, F.; Harker, D. The Crystal Structure of Rhombohedral Acetamide. J. Am. Chem. Soc. 1940, 62, 2008-2019.
73. NIST Chemistry WebBook: http://webbook.nist.gov/chemistry.
74. Ataka, S.; Takeuchi, H.; Tasumi, M. Infrared studies of the less stable eis form of N-Methylformamide and N-Methylacetamide in lowtemperature nitrogen matrices and vibrational analyses of the trans and cis forms of these molecules. J. Mol. Struct. 1984, 773, 147-160.
75. Miyazawa, T. Normal Vibrations of Monosubstituted Amides in the cis Configuration and Infrared Spectra of Diketopiperazine. J. Mol. Spectrosc. 1960, 4, 155-167.
76. Hallam, H. E.; Jones, C. M. Molecular Configuration and Interactions of the Amide Group. Trans. Faraday Soc. 1969, 65, 2607-2610.
77. Kitano, M.; Kuchitsu, K. Molecular Structure of N-Methylformamide as Studied by Gas Electron Diffraction. Bull. Chem. Soc. Jpn. 1974, 47, 631-634.
78. Jones, R. L. The Infrared Spectra of Some Simple N-Substituted Amides in the Vapor State. J. Mol. Spectrosc. 1963, 77, 411 -4-21.
79. Nandini, G.; Sathyanarayana, D. N. Ab initio studies on geometry and vibrational spectra of N-methylformamide and N-methylacetamide. J. Mol. Struct. (Theochem) 2002, 579, 1-9.
80. Martinez, A. G.; Vilar, E. T.; Fraile, A. G.; Martinez-Ruiz, P. A Computational and Experimental Study on the Relative Stabilities of Cis and Trans Isomers of N-Alkylamides in Gas Phase and in Solution. J. Phys. Chem. A 2002, 706, 4942-4950.
81. Scheurer, C.; Piryatinski, A.; Mukamel, S. Signatures of β-peptide unfolding in two-dimensional vibrational echo spectroscopy: A simulation study. J. Am. Chem. Soc. 2001, 123, 3114-3124.
82. Martínez, A. G.; Vilar, E. T.; Fraile, A. G.; Martínez- Ruiz, P. Density functional theory study of self-association of N-methylformamide and its effect on intramolecular and intermolecular geometrical parameters and the cis/trans population. J. Chem. Phys. 2006, 124, 324305.
83. LaPlanche, L. A.; Rogers, M. T. cis and trans Configuration of the Peptide Bond in N-Monosubstituted Amides by Nuclear Magnetic Resonance. J. Am. Chem. Soc. 1964, 86 (3), 337-341.
84. Ludwig, R.; Weinhold, F.; Farrar, T. C. Theoretical Study of hydrogen bonding in liquid and gaseous N-methylformamide. J. Chem. Phys. 1997, 107 (2), 499-507.
85. Woutersen, S.; Mu, Y.; Stock, G.; Hamm, P. Hydrogen-bond lifetime measured by time-resolved 2D-IR spectroscopy: N-methylacetamide in methanol. Chem. Phys. 2001, 266, 137-147.
86. Jorgensen, W. L.; Gao, J. Cis-Trans Energy Difference for the Peptide Bond in the Gas Phase and in Aqueous Solution. J. Am. Chem. Soc. 1988, 110, 4212-4216.
87. Bednárová, L.; Malón, P.; Bour, P. Spectroscopic Properties of the Nonpolar Amide Group: A Computational Study. Chirality 2007, 79, 775-786.
88. Ham, S.; Cho, M. Amide I modes in the N-methylacetamide dimer and glycine dipeptide analog: Diagonal force constants. J. Chem. Phys. 2003, 118 (15), 6915-6922.
89. Ludwig, R.; Reis, O.; Winter, R.; Weinhold, F.; Farrar, T. C. Quantum Cluster Equilibrium Theory of Liquids: Temperature Dependence of Hydrogen Bonding in Liquid N-Methylacetamide Studied by IR Spectra. J. Phys. Chem. B 1998, 102, 9312-9318.
90. Huelsekopf, M.; Ludwig, R. Correlations between structural, NMR and IR spectroscopic properties of N-methylacetamide. Magn. Reson. Chem. 2001, 39, S127-S134.
91. Watson, T. M.; Hirst, J. D. Calculating vibrational frequencies of amides: From formamide to concanavalin A. Phys. Chem. Chem. Phys. 2004, 6, 998-1005.
92. Langley, C. H.; Allinger, N. L. Molecular Mechanics (MM4) and ab Initio Study of Amide-Amide and Amide-Water Dimers. J. Phys. Chem. A 2003, 107, 5208-5216.
93. Wassermann, T. N.; Zielke, P.; Lee, J. J.; Cézard, C.; Suhm, M. A. Structural preferences, argon nanocoating, and dimerization of n-alkanols as revealed by OH stretching spectroscopy in supersonic jets. J. Phys. Chem. A 2007, 111, 7437-7448.
94. Tam, C. N.; Bour, P.; Eckert, J.; Trouw, F. R. Inelastic Neutron Scattering Study of Hydrogen-Bonded Solid Formamide at 15 K. J. Phys. Chem. A 1997, 101, 5877-5884.
95. Torii, H.; Tasumi, M. Intermolecular Hydrogen Bonding and LowWave-Number Vibrational Spectra of Formamide, N-Methylformamide, and N-Methylacetamide in the Liquid State. Int. J. Quantum Chem. 1998, 70, 241-252.
96. Engdahl, A.; Nelander, B.; Astrand, P.-O. Complex formation between water and formamide. J. Chem. Phys. 1993, 99, 4894-4907.
97. Miyazawa, T.; Shimanouchi, T.; Mizushima, S-I. Characteristic Infrared Bands of Monosubstituted Amides. J. Chem. Phys. 1956, 24 (2), 408-418.