Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH14135
RESEARCH ARTICLE
Contents Vol 67(9)

Synthesis, Structures, and Conformations of Linked Bis-Glyoxylamides Derived from Bis-Acylisatins

Venty Suryanti A B , Glenn C. Condie A , Mohan Bhadbhade C , Roger Bishop A , David StC. Black A D and Naresh Kumar A D
+ Author Affiliations
- Author Affiliations

A School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.

B Current address: Department of Chemistry, The University of Sebelas Maret, Surakarta, Jawa Tengah 57126, Indonesia.

C Mark Wainwright Analytical Centre, The University of New South Wales, Sydney, NSW 2052, Australia.

D Corresponding authors. Email: d.black@unsw.edu.au; n.kumar@unsw.edu.au

Australian Journal of Chemistry 67(9) 1270-1278 https://doi.org/10.1071/CH14135
Submitted: 11 March 2014  Accepted: 16 April 2014   Published: 19 May 2014

Abstract

A series of bis-glyoxylamides possessing hydrophobic alkyl chains was successfully synthesised by ring opening of bis-acylisatins with amines or amino acid alkyl esters. The crystal structures revealed the interplay of intra- and intermolecular interactions (NH···O and C=O···C=O interactions) and the conformations of these long molecules.


References

[1]  G. R. Desiraju, Crystal Engineering: The Design of Organic Solids 1989 (Elsevier: Amsterdam).

[2]  J. Hauck, K. Mika, Cryst. Eng. 2002, 5, 105.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xoslalur8%3D&md5=156b61daba6021995f6d48d1c665c87fCAS |

[3]  C. V. K. Sharma, Cryst. Growth Des. 2002, 2, 465.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XmslWju7c%3D&md5=5ae96e06dbeb0d5355b462fab84355e7CAS |

[4]  T. Tanaka, T. Tasaki, Y. Aoyama, J. Am. Chem. Soc. 2002, 124, 12453.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XntlOqsrw%3D&md5=2eca9e6eb0313deb47480ee0f1fefaaeCAS | 12381186PubMed |

[5]  G. R. Desiraju, Acc. Chem. Res. 2002, 35, 565.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xjt1Ojsrs%3D&md5=277f3de5cfabed7b46b4d851e296696bCAS | 12118996PubMed |

[6]  S. Apel, M. Lennartz, L. R. Nassimbeni, E. Weber, Chem. – Eur. J. 2002, 8, 3678.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xmslequ7o%3D&md5=556204829ae0dcc181dd8409f4a7d5f8CAS | 12203295PubMed |

[7]  B. Moulton, J. J. Lu, R. Hajndl, S. Hariharan, M. J. Zaworotko, Angew. Chem. Int. Ed. 2002, 41, 2821.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xmt1emsrg%3D&md5=2e5dd6d6c36665fd357ef75df7211cddCAS |

[8]  S. Kim, R. Bishop, D. C. Craig, I. G. Dance, M. L. Scudder, J. Org. Chem. 2002, 67, 3221.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xis12gur0%3D&md5=61adfe8a097074c271ccd139414e7136CAS | 12003528PubMed |

[9]  A. Raghavanpillai, S. Reinartz, K. W. Hutchenson, J. Fluor. Chem. 2009, 130, 410.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjsl2isr4%3D&md5=833b63ee13d393dbc2557e9909f7c8bcCAS |

[10]  J. Brinksma, B. L. Feringa, R. M. Kellogg, R. Vreeker, J. H. van Esch, Langmuir 2000, 16, 9249.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXns1Sqsbs%3D&md5=97cca6ffc7c53ec1a92c7263a1e74424CAS |

[11]  W. Edwards, C. A. Lagadec, D. K. Smith, Soft Matter 2011, 7, 110.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsFKis77E&md5=64157a263f15800ae3d3d58b1d2af021CAS |

[12]  L. S. Reddy, S. Basavoju, V. R. Vangala, A. Nangia, Cryst. Growth Des. 2006, 6, 161.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtFKltbvE&md5=dbb293af2d0e8ccbd02a974f4b2b2452CAS |

[13]  F. S. Schoonbeek, J. H. van Esch, R. Hulst, R. M. Kellogg, B. L. Feringa, Chem. – Eur. J. 2000, 6, 2633.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXltFCrtr8%3D&md5=ca198d59bf58e1ea0c203cdb4b138928CAS | 10961408PubMed |

[14]  Z. Feng, A. Fan, S. Valiyaveettil, J. J. Vittal, Cryst. Growth Des. 2003, 3, 555.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXjvFOhsbk%3D&md5=be1eae189a5b95983c94fc704d3a6d14CAS |

[15]  R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXntlGntbg%3D&md5=9b0e4e647aad9b422e5407a5dade8bb3CAS | 11710070PubMed |

[16]  S. H. Gellman, Acc. Chem. Res. 1998, 31, 173.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXhvF2qtr0%3D&md5=762800b10de5f9ac3c3b4a8b2c62595dCAS |

[17]  R. R. Gardner, L. A. Christianson, S. H. Gellman, J. Am. Chem. Soc. 1997, 119, 5041.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXjt1Cgtr0%3D&md5=70d9b4419e648efca94185afa8b0573bCAS |

[18]  G. B. Liang, J. M. Desper, S. H. Gellman, J. Am. Chem. Soc. 1993, 115, 925.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXhtVWntbo%3D&md5=ad6eeda0746dda0fffa7ebf8555c2e2eCAS |

[19]  S. H. Gellman, B. R. Adams, G. P. Dado, J. Am. Chem. Soc. 1990, 112, 460.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXns1SnsA%3D%3D&md5=1670b0d4fd849d53aced1187a77c9b4fCAS |

[20]  J. F. Malone, C. M. Murray, M. Nieuwenhuyzen, G. Stewart, R. Docherty, A. J. Lavery, Chem. Mater. 1997, 9, 334.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXht1Ojs7k%3D&md5=7d4db9f4f8b0af73b4008c0fe8404120CAS |

[21]  W. C. Cheah, K. Wood, D. StC. Black, N. Kumar, Tetrahedron 2011, 67, 7603.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtFSjtLnM&md5=568dca0540e10468aa880134c60af03dCAS |

[22]  V. Suryanti, M. Bhadbhade, R. Bishop, D. StC. Black, N. Kumar, CrystEngComm 2012, 14, 7345.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhsVCgu7zI&md5=ef102cb2e16157a1f0ccebf3840cc52dCAS |

[23]  V. Suryanti, M. Bhadbhade, R. Bishop, D. StC. Black, N. Kumar, Tetrahedron 2013, 69, 8446.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXht1Sjtb7N&md5=115ecff359ca1d21546dc1dda63c62edCAS |

[24]  D. StC. Black, G. I. Moss, Aust. J. Chem. 1987, 40, 143.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2sXks12mt7s%3D&md5=20ede02aff419d9586cbe0b27c205f40CAS |

[25]  H. J. Choi, M. O. Kwak, H. Song, Synth. Commun. 1997, 27, 1273.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXitlGit7o%3D&md5=9f720a45a78df393a6d22b9104bd2263CAS |

[26]  E. A. Mash, K. A. Nelso, S. V. Deusen, S. B. Hemperly, Org. Synth. 1989, 68, 92.

[27]  Crystals of 9 were obtained from methanol. Crystal data: C32H40.67N4O6, MW 577.35, Monoclinic, P21/c. Cell dimensions: a 9.1920 (18), b 23.833 (5), c 21.695 (4) Å and β 98.59 (3°), Z 6, T 100 K. Dcalcd 1.224 Mg m–3. Data/restraints/parameters 8258:48:612. Final R indices, R[F2 > 2s(F2)] = 0.090, wR(F2) = 0.252. CCDC 958544.

[28]  Crystals of 24 were obtained from methanol. Crystal data: C24H26N4O6, MW 466.49, Monoclinic, P21. Cell dimensions: a 9.1500 (18), b 14.679 (3), c 9.3670 (19) Å and β 114.43 (3)°, Z 2, T 100 K. Dcalcd 1.353 Mg m–3. Data/restraints/parameters 3311:1:310. Final R indices, R[F2 > 2s(F2)] = 0.042, wR(F2) = 0.113. CCDC 957127.

[29]  Crystals of 25 were obtained from methanol. Crystal data: C30H38N4O6, MW 550.64, Monoclinic, P21/c. Cell dimensions: a 8.9927 (18), b 9.941 (2), c 16.474 (3) Å and β 102.128 (11)°, Z 4, T 150 K. Dcalcd 1.270 Mg m–3. Data/restraints/parameters 2522:0:184. Final R indices, R[F2 > 2s(F2)] = 0.058, wR(F2) = 0.164. CCDC 957125.

[30]  Crystals of 26 were obtained from methanol. Crystal data: C30H38N4O6, MW 550.64, Triclinic, P¯1. Cell dimensions: a 8.9717 (4), b 9.1948 (4), c 9.6574 (4) Å and α 64.779 (2)°, β 81.225 (2)°, γ 89.513 (2)°, Z = 1, T = 150 K. Dcalcd 1.286 Mg m–3. Data/restraints/parameters 2462:0:182. Final R indices, R[F2 > 2s(F2)] = 0.035, wR(F2) = 0.096. Crystallographic data excluding structure factors have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 957126. A copy of the data can be obtained free of charge from CCDC, 12 Union Road, Cambridge CB2 1EZ, UK or e-mail: deposit@ccdc.cam.ac.uk.

[31]  F. H. Allen, C. A. Baalham, J. P. M. Lommerse, P. R. Raithby, Acta Crystallogr. B 1998, 54, 320.
         | Crossref | GoogleScholarGoogle Scholar |

[32]  Bruker, SADABS 2001 (Bruker AXS Inc.: Madison, WI).

[33]  Bruker, APEX2 and SAINT 2001 (Bruker AXS Inc.: Madison, WI).

[34]  G. M. Sheldrick, Acta Crystallogr. 2008, A64, 112.
         | Crossref | GoogleScholarGoogle Scholar |

[35]  C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, P. A. Wood, J. Appl. Cryst. 2008, 41, 466.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXjt1Gmtb0%3D&md5=769cfd323e07ca2653f64f077bf0719bCAS |

[36]  W. Kabsch, J. Appl. Cryst. 1993, 26, 795.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXptFeltw%3D%3D&md5=9419610f4cb6fb932fb5c42cc5bcbb43CAS |