Three-component conformational equilibria of some flexible pyrrolidin-2-(thi)ones in solution by NMR data (δC, δh, and nJHH) and their DFT predictions: A confrontation of different approaches

Tetrahedron

Volumn 67, Issue 36, 2011, Pages 6901-6916

  Nazarski, Ryszard B ^a   Pasternak, Beata ^a   Leśniak, Stanisław ^a  

^a UNIVERSITY OF LODZ   (Poland)

Author keywords

Conformational distribution; DP4 'probability' analysis; GIAO method; Grimme's DFT D3; IEF PCM and COSMO solvation model; Karplus equation; London dispersion forces; Scaling factor; WC04, WP04, and B2PLYP functionals

Indexed keywords

GAMMA LACTAM DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONFORMATION; DENSITY FUNCTIONAL THEORY; DISPERSION; ENERGY; GAS ANALYSIS; ISOELECTRIC FOCUSING; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 80051548664     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.06.095     Document Type: Article

References (166)

1. For a comprehensive list of references see R.M. Aminova, G.A. Schamov, and A.V. Aganov J. Mol. Struct. (Theochem) 498 2000 233 246 and Refs 30-41 cited therein
2. T. Helgaker, M. Jaszuński, and K. Ruud Chem. Rev. 99 1999 293 352
3. P. Tähtinen, A. Bagno, K.D. Klika, and K. Pihlaja J. Am. Chem. Soc. 125 2003 4609 4618 and refs therein
4. M. Kaupp, M. Bühl, and V.G. Malkin Calculation of NMR and EPR Parameters. Theory and Applications 2004 Wiley-VCH Weinheim, Germany
5. T. Helgaker, M. Jaszuński, and M. Pecul Prog. Nucl. Magn. Reson. Spectrosc. 53 2008 249 268 and refs therein
6. E. Michalik, and R.B. Nazarski Tetrahedron 60 2004 9213 9222
7. R.B. Nazarski J. Phys. Org. Chem. 22 2009 834 844
8. R.B. Nazarski Tetraazacyclotetradecane Species as Models of the Polyazacrown Macrocycles (Chemistry Research and Applications Series) 2010 Nova Science New York, NY pp 46-48
9. D.A. Forsyth, and A.B. Sebag J. Am. Chem. Soc. 119 1997 9483 9494 and refs therein
10. A.B. Sebag, C.J. Friel, R.N. Hanson, and D.A. Forsyth J. Org. Chem. 65 2000 7902 7912
11. A.B. Sebag, D.A. Forsyth, and M.A. Plante J. Org. Chem. 66 2001 7967 7973
12. P. Bouř, V. Sychrovský, P. Maloň, J. Hanzlíková, V. Baumruk, J. Pospíšek, and M. Budšinský J. Phys. Chem. A 106 2002 7321 7327
13. G. Barone, D. Duca, A. Silvestri, L. Gomez-Paloma, R. Riccio, and G. Bifulco Chem. - Eur. J. 8 2002 3240 3245
14. P. Cimino, G. Bifulco, A. Evidente, M. Abouzeid, R. Riccio, and L. Gomez-Paloma Org. Lett. 4 2002 2779 2782 and refs therein
15. W. Migda, and B. Rys J. Org. Chem. 71 2006 5498 5506
16. C. Fattorusso, E. Stendardo, G. Appendino, E. Fattorusso, P. Luciano, A. Romano, and O. Taglialatela-Scafati Org. Lett. 9 2007 2377 2380
17. A.M. Belostotskii J. Org. Chem. 73 2008 5723 5731
18. E. Fattorusso, P. Luciano, A. Romano, O. Taglialatela-Scafati, G. Appendino, M. Borriello, and C. Fattorusso J. Nat. Prod. 71 2008 1988 1992
19. M. Cygler, K. Dobrynin, M.J. Grabowski, R.B. Nazarski, and R. Skowroński J. Chem. Soc., Perkin Trans. 2 1985 1495 1501
20. R.B. Nazarski, and R. Skowroński Pol. J. Chem. 77 2003 415 426
21. D. Sroczyński, A. Grzejdziak, and R.B. Nazarski J. Inclusion Phenom. Macrocyclic Chem. 35 1999 251 260
22. R.B. Nazarski Magn. Reson. Chem. 41 2003 70 74 and refs therein
23. Pasternak, B. Ph.D. Thesis, University of Łódź, Łódź, 2002
24. S. Leśniak, and B. Pasternak Tetrahedron Lett. 46 2005 3093 3095
25. S. Leśniak, R.B. Nazarski, and B. Pasternak Tetrahedron 65 2009 6364 6369
26. R.B. Nazarski, and S. Leśniak Bull. Pol. Acad. Sci., Chem. 48 2000 19 25 and refs therein
27. G. Barone, L. Gomez-Paloma, D. Duca, A. Silvestri, R. Riccio, and G. Bifulco Chem. - Eur. J. 8 2002 3233 3239 and refs therein
28. N. Matsumori, M. Murata, and K. Tachibana Tetrahedron 51 1995 12229 12238
29. N. Matsumori, D. Kaneno, M. Murata, H. Nakamura, and K. Tachibana J. Org. Chem. 64 1999 866 876 and refs therein
30. C. Bassarello, P. Cimino, L. Gomez-Paloma, R. Riccio, and G. Bifulco Recent Res. Dev. Org. Chem. 7 2003 219 239
31. G. Bifulco, P. Dambruoso, L. Gomez-Paloma, and R. Riccio Chem. Rev. 107 2007 3744 3779
32. S.G. Smith, and J.M. Goodman J. Org. Chem. 74 2009 4597 4607
33. S. Di Micco, M.G. Chini, R. Riccio, and G. Bifulco Eur. J. Org. Chem. 2010 1411 1434
34. S.G. Smith, and J.M. Goodman J. Am. Chem. Soc. 132 2010 12946 12959
35. O.L. Malkina, D.R. Salahub, and V.G. Malkin J. Chem. Phys. 105 1996 8793 8800
36. M. Stahl, U. Schopfer, G. Frenking, and R.W. Hoffmann J. Org. Chem. 62 1997 3702 3704
37. V. Sychrovský, J. Gräfenstein, and D. Cremer J. Chem. Phys. 113 2000 3530 3547
38. A. Bagno Chem. - Eur. J. 7 2001 1652 1661 and refs therein
39. A. Bagno, F. Rastrelli, and G. Saielli J. Phys. Chem. A 107 2003 9964 9973
40. A. Wu, D. Cremer, A.A. Auer, and J. Gauss J. Phys. Chem. A 106 2002 657 667
41. A. Wu, and D. Cremer Int. J. Mol. Sci. 4 2003 158 192
42. K.K. Baldridge, and J.S. Siegel J. Phys. Chem. A 103 1999 4038 4042
43. D. Colombo, P. Ferraboschi, F. Ronchetti, and L. Toma Magn. Reson. Chem. 40 2002 581 588
44. W. Migda, and B. Rys Magn. Reson. Chem. 42 2004 459 466
45. P. Cimino, L. Gomez-Paloma, D. Duca, R. Riccio, and G. Bifulco Magn. Reson. Chem. 42 2004 S26 S33
46. K.W. Wiitala, T.R. Hoye, and C.J. Cramer J. Chem. Theory Comput. 2 2006 1085 1092
47. F. Jensen J. Chem. Theory Comput. 4 2008 719 727
48. R. Jain, T. Bally, and P.R. Rablen J. Org. Chem. 74 2009 4017 4023
49. T. Kupka, M. Stachów, M. Nieradka, J. Kaminsky, and T. Pluta J. Chem. Theory Comput. 6 2010 1580 1589 J-couplings
50. F. Jensen J. Chem. Theory Comput. 2 2006 1360 1369 and refs therein
51. T. Kupka Magn. Reson. Chem. 47 2009 674 683
52. B. Mennucci, and J. Tomasi J. Chem. Phys. 106 1997 5151 5158
53. E. Cancs, B. Mennucci, and J. Tomasi J. Chem. Phys. 107 1997 3032 3041
54. B. Mennucci, E. Cancs, and J. Tomasi J. Phys. Chem. B 101 1997 10506 10517
55. M. Cossi, V. Barone, B. Mennucci, and J. Tomasi Chem. Phys. Lett. 286 1998 253 260
56. J. Tomasi, B. Mennucci, and E. Cancs J. Mol. Struct. (Theochem) 464 1999 211 226
57. D.B. Chesnut K.B. Lipkowitz, D.B. Boyd, The Ab Initio Computation of Nuclear Magnetic Resonance Chemical Shielding Reviews in Computational Chemistry Vol. 8 1996 VCH New York, NY 245 297
58. M. Barfield, and P. Fagerness J. Am. Chem. Soc. 119 1997 8699 8711
59. B. Ośmiałowski, E. Kolehmainen, and R. Gawinecki Magn. Reson. Chem. 39 2001 334 340
60. N.J.R. van Eikema Hommes, and T. Clark J. Mol. Model. 11 2005 175 185
61. A. Aiello, E. Fattorusso, P. Luciano, A. Mangoni, and M. Menna Eur. J. Org. Chem. 2005 5024 5030
62. A. Bagno, F. Rastrelli, and G. Saielli Chem. - Eur. J. 12 2006 5514 5525 and refs therein
63. K.W. Wiitala, C.J. Cramer, and T.R. Hoye Magn. Reson. Chem. 45 2007 819 829 and refs therein
64. S.G. Smith, R.S. Paton, J.W. Burton, and J.M. Goodman J. Org. Chem. 73 2008 4053 4062
65. K. Dybiec, and A. Gryff-Keller Magn. Reson. Chem. 47 2009 63 66 and refs therein
66. A.E. Aliev, D. Courtier-Murias, and S. Zhou J. Mol. Struct. (Theochem) 893 2009 1 5
67. E.Y. Pankratyev, A.R. Tulyabaev, and L.M. Khalilov J. Comput. Chem. 32 2011 1993 1997
68. M.W. Lodewyk, and D.J. Tantillo J. Nat. Prod. 74 2011 1334 1343 and refs therein
69. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch J. Phys. Chem. 98 1994 11623 11627 and refs therein
70. J.R. Cheeseman, G.W. Truck, T.A. Keith, and M.J. Frisch J. Chem. Phys. 104 1996 5497 5509
71. R.M. Claramunt, C. López, D. Sanz, I. Alkorta, and J. Elguero Heterocycles 55 2001 2109 2121 and refs therein
72. S. Leśniak, A. Chrostowska, D. Kuc, M. Maciejczyk, S. Khayar, R.B. Nazarski, and Ł. Urbaniak Tetrahedron 65 2009 10581 10589
73. H. Lampert, W. Mikenda, A. Karpfen, and H. Kähling J. Phys. Chem. A 101 1997 9610 9617
74. M. Schindler, and W. Kutzelnigg J. Chem. Phys. 76 1982 1919 1933
75. W. Kutzelnigg, U. Fleischer, and M. Schindler P. Diehl, E. Fluck, H. Günther, R. Kosfeld, J. Seelig, NMR - Basic Principles and Progress (Deuterium and Shift Calculation) Vol. 23 1991 Springer Berlin 165 262
76. K. Ruud, T. Helgaker, R. Kobayashi, P. Jørgensen, K.L. Bak, and H.J.A. Jensen J. Chem. Phys. 100 1994 8178 8185
77. T.A. Ruden, O.B. Lutnæs, T. Helgaker, and K. Ruud J. Chem. Phys. 118 2003 9572 9581 and refs therein
78. EMSL Basis Set Library; https://bse.pnl.gov/bse/portal
79. K.L. Schuchardt, B.T. Didier, T. Elsethagen, L. Sun, V. Gurumoorthi, J. Chase, J. Li, and T.L. Windus J. Chem. Inf. Model. 47 2007 1045 1052
80. A. Klamt, and G. Schüürmann J. Chem. Soc., Perkin Trans. 2 1993 799 805
81. A. Klamt, V. Jonas, T. Bürger, and J.C.W. Lohrenz J. Phys. Chem. A 102 1998 5074 5085
82. D.M. Chipman Theor. Chem. Acc. 107 2002 80 89 and refs therein
83. S. Sinnecker, A. Rajendran, A. Klamt, M. Diedenhofen, and F. Neese J. Phys. Chem. A 110 2006 2235 2245
84. V.M. Rayón, and J.A. Sordo J. Chem. Phys. 122 2005 204303-1 204303-8
85. P. Duffy, J.A. Sordo, and F. Wang J. Chem. Phys. 128 2008 125102-1 125102-10
86. T. Kuppens, K. Vandyck, J. van der Eycken, W. Herrebout, B. van der Veken, and P. Bultinck Spectrochim Acta A 67 2007 402 411 (VCD data)
87. M. Kwit, M.D. Rozwadowska, J. Gawroński, and A. Grajewska J. Org. Chem. 74 2009 8051 8063 (ECD data)
88. T. Sato, N. Chono, H. Ishibashi, and M. Ikeda J. Chem. Soc., Perkin Trans. 1 1995 1115 1120
89. J.B. Foresman, and Æ. Frisch Exploring Chemistry with Electronic Structure Methods 2nd ed. 1996 Gaussian Pittsburgh, PA 15106 Chapter 4+Errata
90. Irikura, K. K. Computational Thermochemistry: Prediction and Estimation of Molecular Thermodynamics; Irikura, K. K., Frurip, D. J., Eds. ACS Symposium Series 677; American Chemical Society: Washington, DC, 1998, Appendix B. Essential Statistical Thermodynamics (Errata corrected through January 19, 2001).
91. A.P. Scott, and L. Radom J. Phys. Chem. 100 1996 16502 16513 and refs therein
92. L.A. Curtiss, K. Raghavachari, P.C. Redfern, and J.A. Pople Chem. Phys. Lett. 270 1997 419 426 and refs therein
93. V. Barone J. Chem. Phys. 120 2004 3059 3065
94. P. Sinha, S.E. Boesch, C. Gu, R.A. Wheeler, and A.K. Wilson J. Phys. Chem. A 108 2004 9213 9217
95. K.K. Irikura, R.D. Johnson III, and R.N. Kacker J. Phys. Chem. A 109 2005 8430 8437
96. Chemcraft, Version 1.6 (built 338); http://www.chemcraftprog.com.
97. S.L. Smith Top. Curr. Chem. 27 1972 117 187
98. A.G. Ferrige, and J.C. Lindon J. Magn. Reson. 31 1978 337 340
99. J.C. Lindon, and A.G. Ferrige Prog. Nucl. Magn. Reson. 14 1980 27 66
100. T. Kupka, and J.O. Dzigielewski Magn. Reson. Chem. 26 1988 353 357
101. F.A. Anet, and D.J. O'Leary Tetrahedron Lett. 30 1989 2755 2758
102. O.L. Chapman, and E.D. Hoganson J. Am. Chem. Soc. 86 1964 498 500
103. G.E. Maciel, J.W. McIver Jr. , N.S. Ostlund, and J.A. Pople J. Am. Chem. Soc. 92 1970 1 11 (INDO approximation)
104. D. Jiao, M. Barfield, and V.J. Hruby J. Am. Chem. Soc. 115 1993 10883 10887 (HF methods) and refs therein
105. P.F. Provasi, G.A. Aucar, and S.P.A. Sauer J. Chem. Phys. 115 2001 1324 1334 (ab initio SOPPA methods) and refs therein
106. G. Bifulco, L. Gomez-Paloma, and R. Riccio Tetrahedron Lett. 44 2003 7137 7141 (lactone carbonyl)
107. B. Wang, A.T. Dossey, S.S. Walse, A.S. Edison, and K.M. Merz Jr. J. Nat. Prod. 72 2009 709 713 (ethylenic and carbonyl carbons)
108. A.M. Sarotti, and S.C. Pellegrinet J. Org. Chem. 74 2009 7254 7260
109. J.J. Poza, C. Jiménez, and J. Rodríguez Eur. J. Org. Chem. 2008 3960 3969
110. D.C. Braddock, and H.S. Rzepa J. Nat. Prod. 71 2008 728 730 [OC-O, Cl-C, and Br-C, DFT-mPW1PW91/6-31(d,p)]
111. S.D. Rychnovsky Org. Lett. 8 2006 2895 2898
112. J.N. Woodford, and G.S. Harbison J. Chem. Theory Comput. 2 2006 1464 1475
113. H. Dodziuk, M. Jaszuński, and W. Schilf Magn. Reson. Chem. 43 2005 639 646
114. C.A.G. Haasnoot, F.A.A.M. de Leeuw, and C. Altona Tetrahedron 36 1980 2783 2792
115. E. Kolehmainen, K. Laihia, R. Laatikainen, J. Vepsäläinen, M. Niemitz, and R. Suontamo Magn. Reson. Chem. 35 1997 463 467
116. S. Grimme, J. Antony, S. Ehrlich, and H. Krieg J. Chem. Phys. 132 2010 154104-1 154104-19
117. S. Kristyán, and P. Pulay Chem. Phys. Lett. 229 1994 175 180
118. J. Cioslowski, G. Liu, and D. Moncrieff J. Phys. Chem. A 102 1998 9965 9969
119. S. Grimme Angew. Chem., Int. Ed. 45 2006 4460 4464 and refs therein
120. S. Grimme J. Comput. Chem. 27 2006 1787 1799
121. S. Grimme, J. Antony, T. Schwabe, and C. Mück-Lichtenfeld Org. Biomol. Chem. 5 2007 741 758 and refs therein
122. E.R. Johnson, I.D. Mackie, and G.A. DiLabio J. Phys. Org. Chem. 22 2009 1127 1135
123. F.O. Kannemann, and A.D. Becke J. Chem. Theory Comput. 6 2010 1081 1088
124. J.-W. Song, T. Tsuneda, T. Sato, and K. Hirao Org. Lett. 12 2010 1440 1443
125. S. Grimme Org. Lett. 12 2010 4670 4673
126. C.D. Sherrill J. Chem. Phys. 132 2010 110902-1 110902-7 and refs therein
127. S. Grimme, R. Huenerbein, and S. Ehrlich ChemPhysChem 12 2011 1258 1261
128. Neese, F. and et al., ORCA - An ab initio, DFT and semiempirical SCF-MO package.
129. Version 2.6 Rev. 35 February 29, 2008
130. Version 2.8.0.1 December 12, 2010 University of Bonn Bonn, Germany http://www.thch.ini-bonn.de/tc/orca
131. ® 03, Revision E.01 September 11, 2007 Gaussian 340 Quinnipiac St., Bldg. 40, Wallingford, CT 06492, USA
132. 2=0.9994, SD=0.33 ppm).
133. Nazarski, R. B.; Pasternak, B.; Leśniak, S. VIth Symposium on: Nuclear Magnetic Resonance in Chemistry, Physics and Biological Sciences, Warsaw, Sep 22-24, 2010, poster; Abstracts, P-35.
134. S. Grimme J. Chem. Phys. 124 2006 034108-1 034108-16
135. T. Schwabe, and S. Grimme Phys. Chem. Chem. Phys. 9 2007 3397 3406
136. C.S. López, C. Pérez-Balado, P. Rodríguez- Graña, and Á.R. de Lera Org. Lett. 10 2008 77 80
137. S.M. Koskowich, W.C. Johnson, R.S. Paley, and P.R. Rablen J. Org. Chem. 73 2008 3492 3496
138. All required equations and parameters are implemented in a versatile Java applet available online at http://www-jmg.ch.cam.ac.uk/tools/nmr/DP4.
139. M.J. Riveira, C. Gayathri, A. Navarro-Vázquez, N.V. Tsarevsky, R.R. Gil, and M.P. Mischne Org. Biomol. Chem. 9 2011 3170 3175
140. PCMODEL V 8.5, Molecular Modeling Software for Windows Operating System, Apple Macintosh OS, Linux and Unix August 2003 Serena Software Box 3076, Bloomington, IN 47402-3076, USA
141. M. Saunders J. Am. Chem. Soc. 109 1987 3150 3152
142. M. Saunders, K.N. Houk, Y.-D. Wu, W.C. Still, M. Lipton, G. Chang, and W.C. Guida J. Am. Chem. Soc. 112 1990 1419 1427 and refs therein
143. J.-H. Lii, and N.L. Allinger J. Comput. Chem. 12 1991 186 199
144. M.M. Midland, G. Asirwatham, J.C. Cheng, J.A. Miller, and L.A. Morell J. Org. Chem. 59 1994 4438 4442
145. HyperChem: Molecular Modeling System, Release 8.0.3 for Windows June 2007 Hypercube Gainesville, FL 32601, USA
146. A.D. Becke Phys. Rev. A 38 1988 3098 3100
147. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
148. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
149. B. Miehlich, A. Savin, H. Stoll, and H. Preuss Chem. Phys. Lett. 157 1989 200 206
150. T.A. Halgreen J. Am. Chem. Soc. 114 1992 7827 7843
151. MMFFvdW.par - Van der Waals Parameters; Copyright ÓMerck and Co., Inc., Rahway, New Jersey, USA, 1994, 1995, 1996. All Rights Reserved
152. T.A. Halgreen J. Comput. Chem. 20 1999 730 748 and refs therein
153. Ö Farkas, and H.B. Schlegel J. Chem. Phys. 111 1999 10806 10814 and refs therein
154. A. Bondi J. Phys. Chem. 68 1964 441 451
155. E.B. Wilson Jr. , J.C. Decius, and P.C. Cross Molecular Vibrations: The Theory of Infrared and Raman Vibrational Spectra 1955 McGraw-Hill Book New York, NY
156. A. Schäfer, C. Huber, and R. Ahlrichs J. Chem. Phys. 100 1994 5829 5835
157. F. Weigend, and R. Ahlrichs Phys. Chem. Chem. Phys. 7 2005 3297 3305
158. F. Weigend, and M. Häser Theor. Chem. Acc. 97 1997 331 340
159. F. Weigend, A. Köhn, and C. Hättig J. Chem. Phys. 116 2002 3175 3183
160. F. Weigend, M. Häser, H. Patzelt, and R. Ahlrichs Chem. Phys. Lett. 294 1998 143 152
161. All these basis sets are available for free download from ftp://ftp.chemie.uni-karlsruhe.de/pub/cbasen.
162. S. Huzinaga J. Chem. Phys. 42 1965 1293 1302
163. S. Huzinaga Approximate Atomic Functions. Technical Report. Division of Theoretical Chemistry, Department of Chemistry 1971 University of Alberta Edmonton, Canada
164. R.B. Nazarski Phosphorus, Sulfur Silicon 184 2009 1036 1046
165. A.F.C. Alcântara, D. Piló-Veloso, W.B. De Almeida, C.R.A. Maltha, and L.C.A. Barbosa J. Mol. Struct. 791 2006 180 185
166. U.I. Zakai, A. Błoch-Mechkour, N.E. Jacobsen, L. Abrell, G. Lin, G.S. Nichol, T. Bally, and R.S. Glass J. Org. Chem. 75 2010 8363 8371