Advanced search
Publication Cover
Phosphorus, Sulfur, and Silicon and the Related Elements Volume 189, 2014 - Issue 5
Submit an article Journal homepage
253
Views
10
CrossRef citations to date
0
Altmetric
Original Article

Study of “Racemic Compound-Like” Behavior of Diastereomeric Mixture of Pinanyl Sulfoxides by X-Ray Diffraction, IR Spectroscopy, and DFT Calculations

Valeriya A. StartsevaDepartment of General and Organic Chemistry, Kazan State Medical University, Kazan, Russia
,
Liliya E. NikitinaDepartment of General and Organic Chemistry, Kazan State Medical University, Kazan, RussiaCorrespondence[email protected]; [email protected]
,
Olga A. LodochnikovaX-Ray Department, A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russia
,
Alexander E. KlimovitskiiA.M. Butlerov Chemistry Institute, Kazan (Volga Region) Federal University, Kazan, Russia
,
Alexander V. Aref’evDepartment of General and Organic Chemistry, Kazan State Medical University, Kazan, Russia
,
Nadezhda P. ArtemovaDepartment of General and Organic Chemistry, Kazan State Medical University, Kazan, Russia
,
Andrey V. BodrovDepartment of General and Organic Chemistry, Kazan State Medical University, Kazan, Russia
,
Rashid Z. MusinLaboratory of Physical-Chemical Analysis, A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russia
&
Evgenii N. KlimovitskiiA.M. Butlerov Chemistry Institute, Kazan (Volga Region) Federal University, Kazan, Russia
 show all
Pages 615-629 | Received 10 Jun 2013, Accepted 24 Jul 2013, Published online: 14 May 2014

REFERENCES

  • Brands, K.M. J.; Davies, A.J. Chem. Rev. 2006, 106, 2711-2733.
  • Walker, M.; Pohl, E.; Herbst-Irmer, R.; Gerlitz, M.; Rohr, J.; Sheldrick, G.M. Acta Crystallogr. B. 1999, B55, 607-616.
  • Kostyanovsky, R.G.; Krutius, O.N.; Bronzova, I.A.; Lenev, D.A.; Lyssenko, K.A.; Averkiev, B.В. Mendeleev Commun. 2001, 11, 6-8.
  • Saloutina, L.V.; Zapevalov, A.Y.; Kodess, M.I.; Lyssenko, K.A.; Antipin, M.Y.; Saloutin, V.I.; Chupakhin, O.N. J. Fluor. Chem. 2003, 120, 41-47.
  • Linden, A.; Gunduz, M.G.; Simsek, R.; Safak, C. Acta Crystallogr. Sect. C. 2006, C62, 227-230.
  • Alfonsov, V.A.; Bredikhin, A.A.; Bredikhina, Z.A.; Eliseenkova, R.M.; Kataeva, O.N.; Litvinov, I.A.; Pudovik, M.A. Struct. Chem. 2008, 19, 873-878.
  • Anderson, K.M.; Afarinkia, K.; Yu, H.-W.; Goeta, A.E.; Steed, J.W. Cryst. Growth Des. 2006, 6, 210-213.
  • Wojaczynska, E.; Wojaczynski, J. Chem. Rev. 2010, 110, 4303-4356.
  • Carreno, M.C.; Hernandez-Torres, G.; Ribagorda, M.; Urbano, A. Chem. Commun. 2009, 6129-6144.
  • Arai, Y.; Matsui, M.; Koizumi, T. J. Org. Chem. 1991, 56, 1983-1985.
  • Binns, M.R.; Goodridge, R.J.; Haynes, R.K. Tetrahedron Lett. 1985, 26, 6381-6384.
  • Eschler, B.; Haynes, R.K.; Kremmydas, S. J. Chem. Soc. Chem. Commun. 1988, 12, 137-139.
  • Pyne, S.G.; Bloem, P.; Griffith, R. Tetrahedron Lett. 1989, 45, 7013-7022.
  • Annunziata, R.; Cinquini, M.; Cozzi, F.; Farina, S. Tetrahedron Lett. 1987, 43, 1013-1018.
  • Arai, Y.; Matsui, M.; Koizumi, T. Synthesis 2005, 23, 4321-4325.
  • Vargas-Diaz, M.E.; Rivera, S.L.; Nathan, P.J.; Tamariz, J. Tetrahedron Lett. 2005, 46, 3297-3300.
  • Nikitina, L.E.; Dieva, S.A.; Plemenkov, V.V.; Lodochnikova, O.A.; Gubaidullin, A.T.; Kataeva, O.N.; Litvinov, I.A. Russ. J. Gen. Chem. 2001, 8, 1161-1164.
  • Demakova, M.Ya.; Sudarikov, D.V.; Rubtsova, S.A.; Popov, A.V.; Frolova, L.L.; Slepukhin, P.A.; Kuchin, A.V. Helv. Chim. Acta 2012, 5, 940-950.
  • Demakova, M.Ya.; Sudarikov, D.V.; Rubtsova, S.A.; Slepukhin, P.A.; Kutchin, A.V. Russ. J. Org. Chem. 2012, 1, 113-118.
  • Yang, T.K.; Chen, R.-Y.; Lee, D.-S. J. Org. Chem. 1994, 59, 914-921.
  • Aversa, M.C.; Barattucci, A.; Bonaccorsi, P. ARKIVOC 2002, 17, 79-98.
  • Nikitina, L.E.; Startseva, V.A.; Dieva, S.A.; Vakulenko, I.A.; Shamov, G.A. Chem. Nat. Comp. 2006, 2, 178-181.
  • Aref’ev, A.V.; Startseva, V.A.; Nikitina, L.E.; Lodochnikova, O.A.; Klimovitskii, E.N.; Klimovitskii, A.E. Russ. J. Gen. Chem. 2012, 3, 440-445.
  • Brunet, E.; Garcia Ruano, J.L.; Hoyos, M.A.; Rodríguez, J.H. J. Mol. Struct. 1987, 158, 79-88.
  • Grant, D.J. W. Theory and Origin of Polymorphism. In: H.G. Brittain (Ed.), Polymorphism in Pharmaceutical Solids, Vol. 95; Marcel Dekker Inc.: New York, 1999.
  • Fucke, K.; Qureshi, N.; Yufit, D.S.; Howard, J.A. K.; Steed, J.W. Cryst. Growth Des. 2010, 10, 880-886.
  • Alcudia, F.; Fariña, F.; Garcia Ruano, J.L.; Sánches, F. J. Chem. Soc., Perkin Trans. 2 1978, 412-416.
  • Alcudia, F.; Garcia Ruano, J.L.; Rodríguez, J.H.; Sánches, F. Canad. J. Chem. 1979, 57, 2426-2433.
  • Brunet, E.; Garcia-Ruano, J.L.; Rodríguez, J.H.; Alcudia, F. Tetrahedron 1984, 40, 4433-4445.
  • Brunet, E.; Garcia Ruano, J.L.; Rodríguez, J.H.; Secundino, M.A.; García de la Vega, J.M. J. Mol. Struct. 1986, 144, 109-119.
  • Alcudia, F.; Fernandez, I.; Llera, J.M.; Trujillo, M.; Zorrilla, F. J. Mol. Struct. (Theochem.) 1989, 186, 211-238.
  • Otto, M. Analytische Chemie; WILEY-VCH Verlag GmbH: Weinheim, 2000.
  • Groves, P.; Searle, M.S.; Mackey, J.P.; Williams, D.H. Structure 1994, 2, 747-754.
  • Tietze, L.F.; Eicher, T. Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium; Georg Thieme Verlag: Stuttgart, New York, 1991.
  • Sheldrick, G.M. Acta Crystallogr. 2008, 64, 112-122.
  • Sheldrick, G.M. SHELXL-97 Program for Crystal Structure Refinement; University of Göttingen, Germany, 1997.
  • Spek, A.L. Acta Crystallogr. Sect. A. 1990, s1, c34.
  • Becke, A.D. Phys. Rev., A. 1988, 38, 3098-3100.
  • Lee, C.; Yang, W.; Parr, R.G. Phys. Rev. B. 1988, 37, 785-789.
  • 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, Revision B.01; Gaussian, Inc.: Pittsburgh, PA, 2003.
  • Young, D. Computational Chemistry; Wiley Interscience: New York, 2001.
  • Johnson, C.R.; McCants, D. J. Am. Chem. Soc. 1965, 5, 1109-1114.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.