mPW1PW91 study for conformational isomers of methylene bridge-monosubstituted tetramethoxycalix[4]arenes

Kwangyong Park; Ho-Jun Son; Jong-In Choe

Journal of Industrial and Engineering Chemistry, Vol.20, No.5, 3276-3282, September, 2014

DOI10.1016/j.jiec.2013.12.009 Export Citation

mPW1PW91 study for conformational isomers of methylene bridge-monosubstituted tetramethoxycalix[4]arenes

Kwangyong Park^†, Ho-Jun Son, and Jong-In Choe^†

Department of Chemistry and School of Chemical Engineering and Materials Science, Chung-Ang University, Seoul 156-756, Korea

E-mail:,

Structures of ten conformational isomers of methylene bridge-monosubstituted tetramethoxycalix[4]-arenes, 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetramethoxy-2-ethylcalix[4]arene (1), and methyl 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetramethoxycalix[4]arene-2-carboxylate (2) were optimized by quantum mechanical mPW1PW91/6-31G(d,p) (hybrid Hartree.Fock density functional) calculations. The total electronic and Gibbs free energies of the various conformations (cone, partial cone, 1,2-alternate, and 1,3-alternate) of 1 and 2 were analyzed. The cone (equatorial) and partial cone (equatorial) conformers were disclosed to be the most stable among all the isomers of 1 and 2. The calculated structures agreed well with the experimental results. The IR spectra were calculated at the mPW1PW91/6-31G(d,p) level for the most stable conformer of each methylene bridge-monosubstituted tetramethoxycalix[4]arene.

Keywords:mPW1PW91;Conformer;Methylene bridge-monosubstituted;tetramethoxycalix[4]arene

[References]

Gutsche CD, Calixarenes, Royal Society of Chemistry, Cambridge, 2008.
Mandolini L, Ungaro R (Eds.), Calixarenes in Action, World Scientific Publishers Co., Singapore, 2007.
Vicens J, Asfari Z, Harrowfield JM (Eds.), Calixarenes 50th Anniversary, Kluwer Academic Publishers, Dordrecht, The Netherlands, 1991, Commemorative volume.
Vicens J, Bohmer V (Eds.), Calixarenes: A Versatile Class of Macrocyclic Compounds, Kluwer Academic Publishers, Dordrecht, The Netherlands, 1991.
Ibach S, Prautzsch V, Vogtle F, Chartroux C, Gloe K, Acc. Chem. Res., 32, 729 (1999)
Morohashi N, Narumi F, Iki N, Hattori T, Miyano S, Chem. Rev., 106(12), 5291 (2006)
Columbus I, Biali SE, J. Org. Chem., 73, 2598 (2008)
Columbus I, Biali SE, Org. Lett., 9, 2927 (2007)
Scully PA, Hamilton TM, Bennett JL, Org. Lett., 3, 2741 (2001)
Middel O, Greff Z, Taylor NJ, Verboom W, Reinhoudt DN, Snieckus V, J. Org. Chem., 65, 667 (2000)
Bergamaschi M, Bigi F, Lanfranchi M, Maggi R, Pastorio A, Pellinghelli MA, Peri F, Porta C, Satori G, Tetrahedron, 53, 13037 (1997)
Biali SE, Bohmer V, Cohen S, Ferguson G, Gruttner C, Grynszpan F, Paulus EF, Thondorf I, Vogt W, J. Am. Chem. Soc., 118(51), 12938 (1996)
Podoprygorina G, Janke M, Janshoff A, Bohmer V, Supramol. Chem., 20, 59 (2008)
Breitkreuz CJ, Zadmard R, Schrader T, Supramol. Chem., 20, 109 (2008)
Othman AB, Lee YH, Ohto K, Abidi R, Kim Y, Vicens J, J. Incl. Phenom. Macrocycl. Chem., 62, 187 (2008)
Baklouti L, Cheriaa N, Mahouachi M, Abidi R, Kim JS, Kim Y, Vicens J, J. Incl. Phenom. Macrocycl. Chem., 54, 1 (2006)
Garozzo D, Gattuso G, Notti A, Pappalardo A, Pappalardo S, Parisi MF, Perez M, Pisagatti I, Angew. Chem.-Int. Edit., International ed. 44, 4892 (2005)
Costa AI, Prata JV, Supramol. Chem., 20, 95 (2008)
Jain VK, Pandya RA, Pillai SG, Shrivastav PS, Talanta, 70, 257 (2006)
Vocanson F, Seigle-Ferrand P, Lamartine R, Fort A, Coleman AW, Shahgaldian P, Mugnier J, Zerroukki A, J. Mater. Sci., 13, 1596 (2003)
Baklouti L, Vicens J, Harrowfield J, Calixarenes in the Nanoworld, Springer, Dordrecht, 2007.
Gruber T, Gruner M, Fischer C, Seichter W, Bombicz P, Weber E, New J. Chem., 34, 250 (2010)
Gruner M, Fischer C, Gruber T, Weber E, Supramol. Chem., 22, 256 (2010)
Choe JI, Lee SH, Oh DS, Bull. Kor. Chem. Soc., 25, 55 (2004)
Grootenhuis PDJ, Kollman PA, Groenen LC, Reinhoudt DN, van Hummel GJ, Ugozzoli F, Andreetti GD, J. Am. Chem. Soc., 112, 4165 (1990)
Fischer C, Gruber T, Seichter W, Weber E, Org. Biomol. Chem., 9, 4347 (2011)
Biali SE, Bohmer V, Cohen S, Ferguson G, Gruttner C, Grynszpan F, Paulus EF, Thondorf I, Vogt W, J. Am. Chem. Soc., 118(51), 12938 (1996)
Itzhak N, Biali S, J. Org. Chem., 75, 3437 (2010)
Araki K, Iwamoto K, Shinkai S, Matsuda T, Chem. Lett., 18, 1747 (1989)
Alfieri C, Dradi E, Pochini A, Ungaro R, Gazz. Chim. Ital., 119, 335 (1989)
Simaan S, Biali SE, J. Phys. Org. Chem., 17, 752 (2004)
Kuno L, Biali SE, J. Org. Chem., 76, 3664 (2011)
HyperChem Release 8.0.8, Hypercube, Inc. Waterloo, Ontario, Canada, 2009.
Choe JI, Kim K, Chang SK, Bull. Kor. Chem. Soc., 21, 465 (2000)
Zhao Y, Tishchenko O, Truhlar DG, J. Phys. Org. Chem. B, 109, 19046 (2005)
Adamo C, Barone V, J. Chem. Phys., 108(2), 664 (1998)
Lynch BJ, Fast PL, Harris M, Truhlar DG, J. Chem. Phys. A, 104, 4811 (2000)
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, 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 JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA, Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford CT, 2009.
Foresman JB, Frisch A, Exploring Chemistry with Electronic Structure Methods, 2nd ed., Gaussian, Inc., Pittsburgh, PA, 1996p. 63.
Lee SJ, Chung HY, Kim KS, Bull. Korean Chem. Soc., 25, 1061 (2004)

[Related Articles]

[1] Gutsche CD, Calixarenes, Royal Society of Chemistry, Cambridge, 2008.

[2] Mandolini L, Ungaro R (Eds.), Calixarenes in Action, World Scientific Publishers Co., Singapore, 2007.

[3] Vicens J, Asfari Z, Harrowfield JM (Eds.), Calixarenes 50th Anniversary, Kluwer Academic Publishers, Dordrecht, The Netherlands, 1991, Commemorative volume.

[4] Vicens J, Bohmer V (Eds.), Calixarenes: A Versatile Class of Macrocyclic Compounds, Kluwer Academic Publishers, Dordrecht, The Netherlands, 1991.

[5] Ibach S, Prautzsch V, Vogtle F, Chartroux C, Gloe K, Acc. Chem. Res., 32, 729 (1999)

[6] Morohashi N, Narumi F, Iki N, Hattori T, Miyano S, Chem. Rev., 106(12), 5291 (2006)

[7] Columbus I, Biali SE, J. Org. Chem., 73, 2598 (2008)

[8] Columbus I, Biali SE, Org. Lett., 9, 2927 (2007)

[9] Scully PA, Hamilton TM, Bennett JL, Org. Lett., 3, 2741 (2001)

[10] Middel O, Greff Z, Taylor NJ, Verboom W, Reinhoudt DN, Snieckus V, J. Org. Chem., 65, 667 (2000)

[11] Bergamaschi M, Bigi F, Lanfranchi M, Maggi R, Pastorio A, Pellinghelli MA, Peri F, Porta C, Satori G, Tetrahedron, 53, 13037 (1997)

[12] Biali SE, Bohmer V, Cohen S, Ferguson G, Gruttner C, Grynszpan F, Paulus EF, Thondorf I, Vogt W, J. Am. Chem. Soc., 118(51), 12938 (1996)

[13] Podoprygorina G, Janke M, Janshoff A, Bohmer V, Supramol. Chem., 20, 59 (2008)

[14] Breitkreuz CJ, Zadmard R, Schrader T, Supramol. Chem., 20, 109 (2008)

[15] Othman AB, Lee YH, Ohto K, Abidi R, Kim Y, Vicens J, J. Incl. Phenom. Macrocycl. Chem., 62, 187 (2008)

[16] Baklouti L, Cheriaa N, Mahouachi M, Abidi R, Kim JS, Kim Y, Vicens J, J. Incl. Phenom. Macrocycl. Chem., 54, 1 (2006)

[17] Garozzo D, Gattuso G, Notti A, Pappalardo A, Pappalardo S, Parisi MF, Perez M, Pisagatti I, Angew. Chem.-Int. Edit., International ed. 44, 4892 (2005)

[18] Costa AI, Prata JV, Supramol. Chem., 20, 95 (2008)

[19] Jain VK, Pandya RA, Pillai SG, Shrivastav PS, Talanta, 70, 257 (2006)

[20] Vocanson F, Seigle-Ferrand P, Lamartine R, Fort A, Coleman AW, Shahgaldian P, Mugnier J, Zerroukki A, J. Mater. Sci., 13, 1596 (2003)

[21] Baklouti L, Vicens J, Harrowfield J, Calixarenes in the Nanoworld, Springer, Dordrecht, 2007.

[22] Gruber T, Gruner M, Fischer C, Seichter W, Bombicz P, Weber E, New J. Chem., 34, 250 (2010)

[23] Gruner M, Fischer C, Gruber T, Weber E, Supramol. Chem., 22, 256 (2010)

[24] Choe JI, Lee SH, Oh DS, Bull. Kor. Chem. Soc., 25, 55 (2004)

[25] Grootenhuis PDJ, Kollman PA, Groenen LC, Reinhoudt DN, van Hummel GJ, Ugozzoli F, Andreetti GD, J. Am. Chem. Soc., 112, 4165 (1990)

[26] Fischer C, Gruber T, Seichter W, Weber E, Org. Biomol. Chem., 9, 4347 (2011)

[27] Biali SE, Bohmer V, Cohen S, Ferguson G, Gruttner C, Grynszpan F, Paulus EF, Thondorf I, Vogt W, J. Am. Chem. Soc., 118(51), 12938 (1996)

[28] Itzhak N, Biali S, J. Org. Chem., 75, 3437 (2010)

[29] Araki K, Iwamoto K, Shinkai S, Matsuda T, Chem. Lett., 18, 1747 (1989)

[30] Alfieri C, Dradi E, Pochini A, Ungaro R, Gazz. Chim. Ital., 119, 335 (1989)

[31] Simaan S, Biali SE, J. Phys. Org. Chem., 17, 752 (2004)

[32] Kuno L, Biali SE, J. Org. Chem., 76, 3664 (2011)

[33] HyperChem Release 8.0.8, Hypercube, Inc. Waterloo, Ontario, Canada, 2009.

[34] Choe JI, Kim K, Chang SK, Bull. Kor. Chem. Soc., 21, 465 (2000)

[35] Zhao Y, Tishchenko O, Truhlar DG, J. Phys. Org. Chem. B, 109, 19046 (2005)

[36] Adamo C, Barone V, J. Chem. Phys., 108(2), 664 (1998)

[37] Lynch BJ, Fast PL, Harris M, Truhlar DG, J. Chem. Phys. A, 104, 4811 (2000)

[38] Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, 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 JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA, Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford CT, 2009.

[39] Foresman JB, Frisch A, Exploring Chemistry with Electronic Structure Methods, 2nd ed., Gaussian, Inc., Pittsburgh, PA, 1996p. 63.

[40] Lee SJ, Chung HY, Kim KS, Bull. Korean Chem. Soc., 25, 1061 (2004)