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DFT study of guest-responsive cooperative effects: Inclusion complexation of alcohols with calix[4]pyrrole

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Abstract

Herein, we report guest-responsive structural changes and cooperative effects in inclusion complexes of meso-octamethylcalix[4]pyrrole. A series of lower alcohol guests were modeled using the density functional theory at B97D/6-311 + G* and ωB97D/6-311 + G* level of approximation to study their thermochemical properties and complexation geometries. Results of binding energies of CP:1-alcohol and CP:2-alcohol complexes indicated that the methylene glycol exhibited strongest binding, whereas ethane-1,2-diol has the highest cooperative effects. Attempts were also made to address the cooperative effects by correlating them with the partial charges (Hirshfeld, Atomic Dipole Corrected Hirshfeld) and the second-order energy interactions.

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References

  1. Baeyer A (1886) Ber Dtsch Chem Ges 19:2184

    Article  Google Scholar 

  2. Gale PA, Sessler JL, Kral V, Lynch V (1996) J Am Chem Soc 118:5140

    Article  CAS  Google Scholar 

  3. Custelcean R, Delmau LH, Moyer BA, Sessler JL, Cho WS, Gross D, Bates GW, Brooks SJ, Light ME, Gale PA (2005) Angew Chem 117:2593

    Article  Google Scholar 

  4. Miyaji H, An D, Sessler JL (2001) Supramol Chem 13:661

    Article  CAS  Google Scholar 

  5. Sato W, Miyaji H, Sessler JL (2000) Tetrahedron Lett 41:6731

    Article  CAS  Google Scholar 

  6. Sessler JL, Gebauer A, Gale PA (1997) Gazz Chim Ital 127:723

    CAS  Google Scholar 

  7. Gale PA, García-Garrido SE, Garric J (2008) Chem Soc Rev 37:151

    Article  CAS  PubMed  Google Scholar 

  8. Lee C-H (2011) Bull Korean Chem Soc 32:768

    Article  CAS  Google Scholar 

  9. Tong CC, Quesada R, Sessler JL, Gale PA (2008) Chem Commun 47:6321

    Article  CAS  Google Scholar 

  10. Wintergerst MP, Levitskaia TG, Moyer BA, Sessler JL, Delmau LH (2008) J Am Chem Soc 130:4129

    Article  CAS  PubMed  Google Scholar 

  11. Aydogan A, Coady DJ, Kim SK, Akar A, Bielawski CW, Marquez M, Sessler JL (2008) Angew Chem Int Ed 47:9648

    Article  CAS  Google Scholar 

  12. Fisher MG, Gale PA, Hiscock JR, Hursthouse MB, Light ME, Schmidtchen FP, Tong CC (2009) Chem Commun 21:3017

    Article  CAS  Google Scholar 

  13. Gross DE, Schmidtchen FP, Antonius W, Gale PA, Lynch VM, Sessler JL (2008) Chemistry 14:7822

    Article  CAS  PubMed  Google Scholar 

  14. Luo M, Ma H, Chen F (2015) J Sep Sci 38:1225

    Article  CAS  PubMed  Google Scholar 

  15. Polášek M, Makrlík E, Kvíčala J, Křížová V, Vaňura P (2018) J Mol Struct 1153:78

    Article  CAS  Google Scholar 

  16. Furusho Y, Aida T (1997) Chem Commun 22:2205

    Article  Google Scholar 

  17. Branná P, Černochová J, Rouchal M, Kulhánek P, Babinský M, Marek R, Nečas M, Kuřitka I, Vícha R (2016) J Org Chem 81:9595

    Article  CAS  PubMed  Google Scholar 

  18. Badjić JD, Nelson A, Cantrill SJ, Turnbull WB, Stoddart JF (2005) Acc Chem Res 38:723

    Article  CAS  PubMed  Google Scholar 

  19. Aakeröy CB, Panikkattu S, Chopade PD, Desper J (2013) CrystEngComm 15:3125

    Article  Google Scholar 

  20. Saha BK, Nangia A, Jaskólski M (2005) CrystEngComm 7:355

    Article  CAS  Google Scholar 

  21. Montis R, Arca M, Aragoni MC, Bauzá A, Demartin F, Frontera A, Isaia F, Lippolis V (2017) Cryst Eng Comm 19:4401

    Article  CAS  Google Scholar 

  22. Ciancaleoni G (2018) Phys Chem Chem Phys 20:8506

    Article  CAS  PubMed  Google Scholar 

  23. Kitov PI, Bundle DR (2003) J Am Chem Soc 125:16271

    Article  CAS  PubMed  Google Scholar 

  24. Boys SF, Bernardi F (1970) Mol Phys 19:553

    Article  CAS  Google Scholar 

  25. Boys S, Bernardi F (2002) Mol Phys 100:65

    Article  Google Scholar 

  26. Athar M, Lone MY, Jha PC (2018) Chem Phys 501:68

    Article  CAS  Google Scholar 

  27. Jeremy K (1995) J Chem Soc Perkin 1(1):2231

    Google Scholar 

  28. Glendening E, Reed A, Carpenter J, Weinhold F (1998) NBO, version 3.1, University of Wisconsin, Madison, WI, 1995

  29. Rajesh P, Kandan P, Sathish S, Manikandan A, Gunasekaran S, Gnanasambandan T, Abiramig SB (2017) J Mol Struct 1137:277

    Article  CAS  Google Scholar 

  30. Weinhold F, Landis CR (2001) Chem Educ Res Pract 2:91

    Article  CAS  Google Scholar 

  31. Landis C, Weinhold F (2013) Inorg Chem 52:5154

    Article  CAS  PubMed  Google Scholar 

  32. Heidar-Zadeh F, Ayers PW, Bultinck P (2014) J Chem Phys 141:094103

    Article  CAS  PubMed  Google Scholar 

  33. Liu S, Rong C, Lu T (2014) J Phys Chem A 118:3698

    Article  CAS  PubMed  Google Scholar 

  34. Zhou X-Y, Rong C-Y, Lu T, Liu S-B (2014) Acta Phys-Chim Sin 30:2055

    CAS  Google Scholar 

  35. Lu T, Chen F (2012) J Theo Comput Chem 11:163

    Article  CAS  Google Scholar 

  36. Allen FH (2002) Acta Cryst B 58:380

    Article  CAS  Google Scholar 

  37. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukud R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JJA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi MR, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts RE, Stratmann O, Yazyev AJ, Austin R, Cammi C, Pomelli JW, Ochterski R, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, revision B.01. Gaussian Inc, Wallingford

  38. Athar M, Das S, Jha PC, Jha AM (2018) Supramol Chem 30:982

    Article  CAS  Google Scholar 

  39. Athar M, Lone MY, Jha PC (2017) J Mol Liq 237:473

    Article  CAS  Google Scholar 

  40. Panchal M, Athar M, Jha P, Kongor A, Mehta V, Jain V (2017) J Lumin 192:256

    Article  CAS  Google Scholar 

  41. de Sousa SM, Fernandes SA, De Almeida WB, Guimarães L, Abranches PA, Varejão EV, Nascimento CS Jr (2016) Chem Phys Lett 646:52

    Article  CAS  Google Scholar 

  42. Chai J-D, Head-Gordon M (2008) Phys Chem Chem Phys 10:6615

    Article  CAS  PubMed  Google Scholar 

  43. Grimme S, Ehrlich S, Goerigk L (2011) J Comput Chem 32:1456

    Article  CAS  PubMed  Google Scholar 

  44. Grimme S (2006) J Comput Chem 27:1787

    Article  CAS  PubMed  Google Scholar 

  45. Suwattanamala A, Magalhaes A, Gomes J (2004) Chem Phys Lett 385:368

    Article  CAS  Google Scholar 

  46. Barone V, Cossi M (1998) J Phys Chem A 102:1995

    Article  CAS  Google Scholar 

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Acknowledgement

The authors gratefully acknowledge the financial support of the Department of Science & Technology (DST), New Delhi, under INSPIRE-SRF Grant (Reg. No. IF150167) awarded to Mohd Athar. Prakash C. Jha would also like to thank SERB, DST, for the project Grant (EMR/2016/003025). Moreover, the Central University of Gujarat-Gandhinagar (CUG) is also greatly acknowledged for providing basic infrastructure and computational facilities.

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Authors and Affiliations

  1. CCG@CUG, School of Chemical Sciences, Central University of Gujarat, Gandhinagar, 380230, Gujarat, India

    Mohd Athar

  2. CCG@CUG, Center of Applied Chemistry, Central University of Gujarat, Gandhinagar Gujarat, 382030, India

    Prakash C. Jha

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  1. Mohd Athar
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  2. Prakash C. Jha
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Correspondence to Prakash C. Jha.

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Athar, M., Jha, P.C. DFT study of guest-responsive cooperative effects: Inclusion complexation of alcohols with calix[4]pyrrole. Monatsh Chem 150, 1205–1214 (2019). https://doi.org/10.1007/s00706-019-02436-0

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  • DOI: https://doi.org/10.1007/s00706-019-02436-0

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