Synthesis of single azo disperse dye containing double ester and determination of crystal structure

Zhengyu Zhang; Hong Xu; Chunling Zheng

Korean Journal of Chemical Engineering, Vol.30, No.12, 2219-2222, December, 2013

DOI10.1007/s11814-013-0167-8 Export Citation

Synthesis of single azo disperse dye containing double ester and determination of crystal structure

Zhengyu Zhang, Hong Xu^†, and Chunling Zheng

College of Food Science and Light Industry, Nanjing University of Technology, Nanjing, Jiangsu 211816, China

E-mail:

The synthesis, crystal structure analysis and characterization of a monoazo dye, 4-((2,6-dichloro-4-nitro phenyl)azo)-N-(diacetyl oxygen ethyl)aniline, are reported. The dye crystallised in the triclinic system, space group P-1 with a=8.1663(3) Å, b= 9.4222(3) Å, c=15.4694(5) Å, α=78.9130(10)°, β=75.019(2)°, γ =70.787(2)°, V=1078.26(6) Å3 and Z=2. There is only one molecule in the asymmetric unit. The dihedral angle between the two phenyl rings is 53.4 Å. In the crystal structure, intermolecular C-H…O hydrogen bonds link the molecules into centrosymmetric dimers, forming R22(30) ring motifs, in which they may be effective in the stabilization of the structure. Between the phenyl rings, the π…π stacking (interactions) may further stabilize the structure.

Keywords:Crystal Structure;Monoazo Dye;Dihedral Angle;Hydrogen Bonds;π…π Stacking

[References]

Scher HB, Rodson M, Lee KS, Pestic. Sci., 54, 394 (1998)
Kim TH, Ko YS, Kwon YK, J. Nanosci. Nanotechnol., 11, 3450 (2006)
Yaroschuk O, Sergan T, Lindau J, Lee SN, Kelly J, Chien LC, J. Chem. Phys., 114(12), 5330 (2001)
Nakamura T, Shibusawa T, Text. Res. J., 70, 801 (2000)
Sakthivel S, Neppolian B, Shankar MV, Arabindoo B, Palanichamy M, Murugesan V, Sol. Energy Mater. Sol. Cells, 77(1), 65 (2003)
Muruganandham M, Swaminathan M, Sol. Energy Mater. Sol. Cell., 84, 439 (2004)
Muruganandham A, Shobana N, Swaminathan A, J. Mol. Catal. A-Chem., 246(1-2), 154 (2006)
Qjan Y, Wang G, Xiao G, Lin B, Cui Y, Dyes Pigm., 75, 460 (2007)
Qju F, Cao Y, Xu H, Jiang Y, Zhou Y, Liu J, Dyes Pigm., 75, 454 (2007)
So BK, Kim HJ, Lee SM, Song HH, Park JH, Dyes Pigm., 70, 38 (2006)
Gimenez R, Millaruelo M, Pinol M, Serrano JL, Vinuales A, Rosenhauer R, Fischer T, Stumpe J, Polymer, 46(22), 9230 (2005)
Ghanadzadeh A, Shahzamanian MA, Shoarinejad S, Zakerhamidi MS, Moghadam M, J. Mol. Liq., 136, 22 (2007)
Viswamathan NK, Kim DY, Bian S, Williams J, Liu W, Liu L, Samuelson L, Kumar J, J. Mater. Chem., 9, 1941 (1999)
Wang AH, Tao C, Cui Y, Duan L, Yang Y, Li JB, J. Colloid Interface Sci., 332(2), 271 (2009)
Yuan L, Liang GZ, Xie JQ, Li L, Guo J, Polymer, 47(15), 5338 (2006)
Yang W, You XL, Zhong Y, Zhang DC, Dyes Pigm., 73, 317 (2007)
Seo J, Jo WJ, Choi G, Park KM, Lee SS, Lee JS, Dyes Pigm., 72, 328 (2007)
Seferoglu Z, Ertan N, Kickelbick G, Hokelek T, Dyes Pigm., 82, 20 (2009)
Singh K, Mahajan A, Robinson WT, Dyes Pigm., 74, 95 (2007)
Lee JE, Kim HJ, Han MR, Lee SY, Jo WJ, Lee SS, Lee JS, Dyes Pigm., 80, 181 (2009)
Jiang W, Tang J, Qi Q, Wu W, Sun Y, Fu D, Dyes and v., 80, 11 (2009)
Singh K, Singh S, Garg PK, Hundal MS, Dyes Pigm., 54, 72 (2004)
Jagadeesh B, Bodapati, Icil H, Dyes Pigm., 79, 224 (2008)
Ozbey S, Karayel A, Kavak G, Sefero luc Z, Ertan N, Color.Technol., 123, 358 (2007)
Singh K, Singh S, Garg PK, Hundal MS, Color. Technol., 120, 72 (2004)
Chang CH, Christie RM, Rosair GM, Dyes Pigm., 82, 147 (2009)
Zandi M, Hashemi SA, Aminayi P, Hosseinali F, J. Appl. Polym. Sci., 119(1), 586 (2011)
Harms K, Wocadlo S, XCAD4, University of Marburg, Germany (1995)
North ACT, Phillips DC, Mathews FS, Acta Crystallogr., A24, 351 (1968)
Sheldrick GM, Acta Crystallogr., A64, 112 (2008)
Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor R, J. Chem. Soc., Perkin Trans., 2, 1 (1987)

[Referenced By]

[1] Scher HB, Rodson M, Lee KS, Pestic. Sci., 54, 394 (1998)

[2] Kim TH, Ko YS, Kwon YK, J. Nanosci. Nanotechnol., 11, 3450 (2006)

[3] Yaroschuk O, Sergan T, Lindau J, Lee SN, Kelly J, Chien LC, J. Chem. Phys., 114(12), 5330 (2001)

[4] Nakamura T, Shibusawa T, Text. Res. J., 70, 801 (2000)

[5] Sakthivel S, Neppolian B, Shankar MV, Arabindoo B, Palanichamy M, Murugesan V, Sol. Energy Mater. Sol. Cells, 77(1), 65 (2003)

[6] Muruganandham M, Swaminathan M, Sol. Energy Mater. Sol. Cell., 84, 439 (2004)

[7] Muruganandham A, Shobana N, Swaminathan A, J. Mol. Catal. A-Chem., 246(1-2), 154 (2006)

[8] Qjan Y, Wang G, Xiao G, Lin B, Cui Y, Dyes Pigm., 75, 460 (2007)

[9] Qju F, Cao Y, Xu H, Jiang Y, Zhou Y, Liu J, Dyes Pigm., 75, 454 (2007)

[10] So BK, Kim HJ, Lee SM, Song HH, Park JH, Dyes Pigm., 70, 38 (2006)

[11] Gimenez R, Millaruelo M, Pinol M, Serrano JL, Vinuales A, Rosenhauer R, Fischer T, Stumpe J, Polymer, 46(22), 9230 (2005)

[12] Ghanadzadeh A, Shahzamanian MA, Shoarinejad S, Zakerhamidi MS, Moghadam M, J. Mol. Liq., 136, 22 (2007)

[13] Viswamathan NK, Kim DY, Bian S, Williams J, Liu W, Liu L, Samuelson L, Kumar J, J. Mater. Chem., 9, 1941 (1999)

[14] Wang AH, Tao C, Cui Y, Duan L, Yang Y, Li JB, J. Colloid Interface Sci., 332(2), 271 (2009)

[15] Yuan L, Liang GZ, Xie JQ, Li L, Guo J, Polymer, 47(15), 5338 (2006)

[16] Yang W, You XL, Zhong Y, Zhang DC, Dyes Pigm., 73, 317 (2007)

[17] Seo J, Jo WJ, Choi G, Park KM, Lee SS, Lee JS, Dyes Pigm., 72, 328 (2007)

[18] Seferoglu Z, Ertan N, Kickelbick G, Hokelek T, Dyes Pigm., 82, 20 (2009)

[19] Singh K, Mahajan A, Robinson WT, Dyes Pigm., 74, 95 (2007)

[20] Lee JE, Kim HJ, Han MR, Lee SY, Jo WJ, Lee SS, Lee JS, Dyes Pigm., 80, 181 (2009)

[21] Jiang W, Tang J, Qi Q, Wu W, Sun Y, Fu D, Dyes and v., 80, 11 (2009)

[22] Singh K, Singh S, Garg PK, Hundal MS, Dyes Pigm., 54, 72 (2004)

[23] Jagadeesh B, Bodapati, Icil H, Dyes Pigm., 79, 224 (2008)

[24] Ozbey S, Karayel A, Kavak G, Sefero luc Z, Ertan N, Color.Technol., 123, 358 (2007)

[25] Singh K, Singh S, Garg PK, Hundal MS, Color. Technol., 120, 72 (2004)

[26] Chang CH, Christie RM, Rosair GM, Dyes Pigm., 82, 147 (2009)

[27] Zandi M, Hashemi SA, Aminayi P, Hosseinali F, J. Appl. Polym. Sci., 119(1), 586 (2011)

[28] Harms K, Wocadlo S, XCAD4, University of Marburg, Germany (1995)

[29] North ACT, Phillips DC, Mathews FS, Acta Crystallogr., A24, 351 (1968)

[30] Sheldrick GM, Acta Crystallogr., A64, 112 (2008)

[31] Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor R, J. Chem. Soc., Perkin Trans., 2, 1 (1987)