Beilstein J. Org. Chem. 2019, 15, 818–829.
9. Kleinpeter, E.; Werner, P.; Linker, T. Tetrahedron 2017, 73,
Supporting Information
10.Eliel, E. L.; Della, E. W.; Williams, T. H. Tetrahedron Lett. 1963, 4,
11.Batchelor, J. G. J. Chem. Soc., Perkin Trans. 2 1976, 1585.
Supporting Information File 1
1H and 13C NMR spectra at 25 and −80 °C, supplementary
theoretical values, RScript for PCA and the Cartesian
coordinates of the structures.
12.Freitas, M. P.; Rittner, R.; Tormena, C. F.; Abraham, R. J.
Spectrochim. Acta, Part A 2005, 61, 1771–1776.
13.Freitas, M. P.; Tormena, C. F.; Rittner, R. J. Mol. Struct. 2001, 570,
14.Basso, E. A.; Abiko, L. A.; Gauze, G. F.; Pontes, R. M. J. Org. Chem.
Supporting Information File 2
NBO data for PCA.
15.Taddei, F.; Kleinpeter, E. J. Mol. Struct.: THEOCHEM 2004, 683,
16.Ribeiro, D. S.; Rittner, R. J. Org. Chem. 2003, 68, 6780–6787.
17.Alabugin, I. V.; Zeidan, T. A. J. Am. Chem. Soc. 2002, 124,
Acknowledgements
18.Taddei, F.; Kleinpeter, E. J. Mol. Struct.: THEOCHEM 2005, 718,
19.de Melo, U. Z.; dos Santos Yamazaki, D. A.; de Araújo Cândido, A.;
Basso, E. A.; de Freitas Gauze, G. J. Mol. Struct. 2018, 1163,
The authors would like to thank the Brazilian Council for Scien-
tific and Technological Development (CNPq) for the fellow-
ships to E.A.B. and R.R., and for the scholarship to C.S.F.; and
the Coordination for the Improvement of Higher Education
Personnel (CAPES) for the scholarships to C.B.F. and U.Z.M.
Thanks also go to the São Paulo Research Foundation
(FAPESP) (Grant 2016/24109-0) for the financial assistance
and to the National Center for High Performance Computing
(CENAPAD-UFC) for the computational cluster disponibility.
20.Lopes Jesus, A. J.; Rosado, M. T. S.; Redinha, J. S.
Comput. Theor. Chem. 2011, 964, 32–39.
21.Alabugin, I. V.; dos Passos Gomes, G.; Abdo, M. A.
Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2019, 9, e1389.
22.Bocca, C. C.; Basso, E. A.; Fiorin, B. C.; Tormena, C. F.;
dos Santos, F. P. J. Phys. Chem. A 2006, 110, 9438–9442.
ORCID® iDs
23.Basso, E. A.; Kaiser, C.; Rittner, R.; Lambert, J. B.
Magn. Reson. Chem. 1994, 32, 205–209.
24.Allinger, N. L.; Pamphilis, N. A. J. Org. Chem. 1973, 38, 316–319.
25.Yoshida, Z.-i.; Nakagawa, K. Tetrahedron Lett. 1965, 6, 3753–3756.
26.Silla, J. M.; Duarte, C. J.; Freitas, M. P.; Ramalho, T. C.;
Cormanich, R. A.; Santos, F. P.; Tormena, C. F.; Rittner, R.
Spectrochim. Acta, Part A 2011, 81, 359–362.
References
1. Eliel, E. L.; Samuel, H. W. Stereochemistry of Organic Compounds;
Wiley-Interscience: New York, 1994.
2. de Oliveira, P. R.; Viesser, R. V.; Guerrero, P. G., Jr.; Rittner, R.
Spectrochim. Acta, Part A 2011, 78, 1599–1605.
27.Basso, E. A.; Kaiser, C.; Rittner, R.; Lambert, J. B. J. Org. Chem. 1993,
28.Silla, J. M.; Cormanich, R. A.; Duarte, C. J.; Freitas, M. P.;
Ramalho, T. C.; Barbosa, T. M.; Santos, F. P.; Tormena, C. F.;
Rittner, R. J. Phys. Chem. A 2011, 115, 10122–10127.
3. de Oliveira, P. R.; Rittner, R. Spectrochim. Acta, Part A 2008, 70,
4. Duarte, C. J.; Freitas, M. P. J. Mol. Struct. 2009, 930, 135–139.
29.Cedran, J. C.; dos Santos, F. P.; Basso, E. A.; Tormena, C. F.
30.de Oliveira, P. R.; Rittner, R. Magn. Reson. Chem. 2008, 46, 250–255.
5. Silla, J. M.; Freitas, M. P. Comput. Theor. Chem. 2012, 999, 89–92.
6. de Oliveira, P. R.; Rittner, R. Spectrochim. Acta, Part A 2005, 61,
31.Reed, A. E.; Weinhold, F. Isr. J. Chem. 1991, 31, 277–285.
7. Onoda, A.; Haruna, H.; Yamamoto, H.; Takahashi, K.; Kozuki, H.;
Okamura, T.-a.; Ueyama, N. Eur. J. Org. Chem. 2005, 641–645.
32.Badenhoop, J. K.; Weinhold, F. J. Chem. Phys. 1997, 107, 5422–5432.
8. Lambert, K. M.; Stempel, Z. D.; Wiberg, K. B.; Bailey, W. F. Org. Lett.
33.Wang, J.; Wolf, R. M.; Caldwell, J. W.; Kollman, P. A.; Case, D. A.
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