321
structure of a series of alkene oxides and mechanism of cleavage of the epoxy ring in acid
media. Osnov Organ Sintez i Neftekhimiya. Yaroslavl 19:82–87
30. Okovityi SI, Platitsyna EL, Kas’yan LI (2001) Theoretical study of alkaline methanolysis of
alicyclic epoxy derivatives. Rus J Org Chem 37(3):345–350
31. Fujimoto H, Hataue S, Koga N, Yamasaki J (1984) Ring-opening of oxirane by nucleophilic
attack. Transition states and paired Interacting Orbitals. Tetrahedron Lett 25(46):5339–5342
32. Lundin A, Panas I, Ahlberg E (2007) A mechanistic investigation of ethylene oxide hydrolysis to ethanediol. J Phys Chem A 111(37):9087–9092
33. Glad SS, Jensen F (1994) Ab initio study of the nucleophilic ring opening of ethylene oxide.
Connection between secondary isotope effects and transition structures. J Chem Soc Perkin
Trans II 4:871–876
34. Scheppele SE (1972) Kinetic isotope effects as a valid measure of structure–reactivity relations. Isotope effects and nonclassical theory. Chem Rev 72(5):511–532
35. Williams IN (1984) Theoretical modelling of compression effects in enzymic methyl transfer.
J Am Chem Soc 106(23):7206–7212
36. Lau EY, Newby ZE, Bruice TC (2001) A theoretical examination of the acid-catalyzed and
noncatalyzed ring-opening reaction of an oxirane by nucleophilic addition of acetate. Implications to epoxide hydrolases. J Am Chem Soc 123(14):3350–3357
37. Kas’yan LI, Stepanova NV, Belyakova TA, Kunanets VK, Lutsenko AI, Zefirov NS (1984)
Methanolysis of cyclic epoxide compounds. Zh Org Khim 20(11):2295–2301
38. Podlogar BL, Raber DJ (1989) Molecular mechanics calculations of epoxides. Extension of
the MM2 force field. J Org Chem 54(21):5032–5035
39. Stewart JJP (1989) Optimization of parameters for semiempirical methods. I. Method. J
Comput Chem 10(2):209–220
40. Klamt A (1995) Conductor-like screening model for real solvents: a new approach to the
quantitative calculation of solvation phenomena. J Phys Chem 7(99):2224–2235
41. Okovytyy SI, Platicina EL, Kasyan LI (1998) Theoretical investigation of the solvent influence on the oxirane alkaline methanolysis mechanism. Visn dnipropetr univ: Khim 2:132–
135
42. Kas’yan LI, Gapanova RG, Okovityi SI (1994) Effect of medium on methanolysis of dicyclopentadiene diepoxide. Zh Org Khim 30(5):692–698
43. Okovytyy SI, Platicina EL, Kasyan LI (2000) Quantum chemical investigation of the environment influence on diepoxide dicyclopentadiene methanolysis. Visn Dnipropetr Univ:
Khim 4:42–47
44. Okovytyy SI, Platicina EL, Seferova MF, Kasyan LI (2001) Theoretical investigation of the
mechanism of spirooxiranes interaction with methanole. Visn Dnipropetr Univ: Khim 6:46–
49
45. Laitinen T, Rouvinen J, Peräkylä M (1998) Ab initio quantum mechanical and density functional theory calculations on nucleophile- and nucleophile and acid-catalyzed opening of an
epoxide ring: a model for the covalent binding of epoxyalkyl inhibitors to the active site of
glycosidases. J Org Chem 63(23):8157–8162
46. Helten H, Schirmeister T, Engels B (2004) Model calculations about the influence of protic
environments on the alkylation step of epoxide, aziridine, and thiirane based cysteine protease inhibitors. J Phys Chem A 108(38):7691–7701
47. Helten H, Schirmeister T, Engels B (2004) Theoretical studies about the influence of different ring substituents on the nucleophilic ring opening of three-membered heterocycles
and possible implications for the mechanisms of cysteine protease inhibitors. J Org Chem
70(1):223–237
48. Meara JP, Rich DH (1996) Mechanistic studies on the inactivation of papain by epoxysuccinyl inhibitors. J Med Chem 39(17):3357–3366
49. Alagona G, Scrocco E, Tomasi J (1979) Theoretical ab initio study of the reaction of formation of 2-fluorethanol. Theor Chim Acta 51(1):11–35
50. Bobylev VA, Koldobskii SG, Tereshchenko GF, Gidaspov BV (1988) Khim Geterotsikl Soedin 9:1155–1168
10 Quantum-Chemical Investigation of Epoxidic Compounds Transformation
structure of a series of alkene oxides and mechanism of cleavage of the epoxy ring in acid
media. Osnov Organ Sintez i Neftekhimiya. Yaroslavl 19:82–87
30. Okovityi SI, Platitsyna EL, Kas’yan LI (2001) Theoretical study of alkaline methanolysis of
alicyclic epoxy derivatives. Rus J Org Chem 37(3):345–350
31. Fujimoto H, Hataue S, Koga N, Yamasaki J (1984) Ring-opening of oxirane by nucleophilic
attack. Transition states and paired Interacting Orbitals. Tetrahedron Lett 25(46):5339–5342
32. Lundin A, Panas I, Ahlberg E (2007) A mechanistic investigation of ethylene oxide hydrolysis to ethanediol. J Phys Chem A 111(37):9087–9092
33. Glad SS, Jensen F (1994) Ab initio study of the nucleophilic ring opening of ethylene oxide.
Connection between secondary isotope effects and transition structures. J Chem Soc Perkin
Trans II 4:871–876
34. Scheppele SE (1972) Kinetic isotope effects as a valid measure of structure–reactivity relations. Isotope effects and nonclassical theory. Chem Rev 72(5):511–532
35. Williams IN (1984) Theoretical modelling of compression effects in enzymic methyl transfer.
J Am Chem Soc 106(23):7206–7212
36. Lau EY, Newby ZE, Bruice TC (2001) A theoretical examination of the acid-catalyzed and
noncatalyzed ring-opening reaction of an oxirane by nucleophilic addition of acetate. Implications to epoxide hydrolases. J Am Chem Soc 123(14):3350–3357
37. Kas’yan LI, Stepanova NV, Belyakova TA, Kunanets VK, Lutsenko AI, Zefirov NS (1984)
Methanolysis of cyclic epoxide compounds. Zh Org Khim 20(11):2295–2301
38. Podlogar BL, Raber DJ (1989) Molecular mechanics calculations of epoxides. Extension of
the MM2 force field. J Org Chem 54(21):5032–5035
39. Stewart JJP (1989) Optimization of parameters for semiempirical methods. I. Method. J
Comput Chem 10(2):209–220
40. Klamt A (1995) Conductor-like screening model for real solvents: a new approach to the
quantitative calculation of solvation phenomena. J Phys Chem 7(99):2224–2235
41. Okovytyy SI, Platicina EL, Kasyan LI (1998) Theoretical investigation of the solvent influence on the oxirane alkaline methanolysis mechanism. Visn dnipropetr univ: Khim 2:132–
135
42. Kas’yan LI, Gapanova RG, Okovityi SI (1994) Effect of medium on methanolysis of dicyclopentadiene diepoxide. Zh Org Khim 30(5):692–698
43. Okovytyy SI, Platicina EL, Kasyan LI (2000) Quantum chemical investigation of the environment influence on diepoxide dicyclopentadiene methanolysis. Visn Dnipropetr Univ:
Khim 4:42–47
44. Okovytyy SI, Platicina EL, Seferova MF, Kasyan LI (2001) Theoretical investigation of the
mechanism of spirooxiranes interaction with methanole. Visn Dnipropetr Univ: Khim 6:46–
49
45. Laitinen T, Rouvinen J, Peräkylä M (1998) Ab initio quantum mechanical and density functional theory calculations on nucleophile- and nucleophile and acid-catalyzed opening of an
epoxide ring: a model for the covalent binding of epoxyalkyl inhibitors to the active site of
glycosidases. J Org Chem 63(23):8157–8162
46. Helten H, Schirmeister T, Engels B (2004) Model calculations about the influence of protic
environments on the alkylation step of epoxide, aziridine, and thiirane based cysteine protease inhibitors. J Phys Chem A 108(38):7691–7701
47. Helten H, Schirmeister T, Engels B (2004) Theoretical studies about the influence of different ring substituents on the nucleophilic ring opening of three-membered heterocycles
and possible implications for the mechanisms of cysteine protease inhibitors. J Org Chem
70(1):223–237
48. Meara JP, Rich DH (1996) Mechanistic studies on the inactivation of papain by epoxysuccinyl inhibitors. J Med Chem 39(17):3357–3366
49. Alagona G, Scrocco E, Tomasi J (1979) Theoretical ab initio study of the reaction of formation of 2-fluorethanol. Theor Chim Acta 51(1):11–35
50. Bobylev VA, Koldobskii SG, Tereshchenko GF, Gidaspov BV (1988) Khim Geterotsikl Soedin 9:1155–1168
10 Quantum-Chemical Investigation of Epoxidic Compounds Transformation