Role of arene interactions and substituent effects in conformational (syn/anti) control of 1,2-diarylethanes

被引:11
作者
Avasthi, Kamlakar [1 ]
Kumar, Amar [1 ]
Aswal, Sangeeta [1 ]
Kant, Ruchir [2 ]
Raghunandan, Resmi [2 ]
Maulik, Prakas R. [2 ]
Khanna, Ranjana S. [3 ]
Ravikumar, Krishnan [4 ]
机构
[1] Cent Drug Res Inst, CSIR, Med & Proc Chem Div, Lucknow 226001, Uttar Pradesh, India
[2] Cent Drug Res Inst, CSIR, Mol & Struct Biol Div, Lucknow 226001, Uttar Pradesh, India
[3] Banaras Hindu Univ, Dept Chem, Varanasi 221005, Uttar Pradesh, India
[4] Indian Inst Chem Technol, CSIR, X Ray Crystallog Div, Hyderabad 500007, Andhra Pradesh, India
关键词
LEONARD LINKER COMPOUNDS; PI-STACKING INTERACTIONS; CENTRAL BOND-LENGTH; CENTER-DOT-PI; CRYSTALLOGRAPHIC EVIDENCE; AROMATIC INTERACTIONS; PROPYLENE-LINKER; MOLECULAR RECOGNITION; FOLDED CONFORMATION; FLEXIBLE MOLECULE;
D O I
10.1039/c1ce06001e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Conformational analysis of nine designed flexible 1,2-diarylethanes with different substituents show syn conformation due to pi-pi interactions by H-1 NMR in solution, this carries over to the solid state for three compounds while two show anti conformation in the solid state by X-ray crystallography and the remaining compounds do not give diffraction quality crystals.
引用
收藏
页码:383 / 388
页数:6
相关论文
共 69 条
[1]   How strong is a pi-facial hydrogen bond? [J].
Adams, H ;
Harris, KDM ;
Hembury, GA ;
Hunter, CA ;
Livingstone, D ;
McCabe, JF .
CHEMICAL COMMUNICATIONS, 1996, (22) :2531-2532
[2]  
[Anonymous], 2011, ANGEW CHEM, DOI DOI 10.1002/ANIE.201007560
[3]  
AVASTHI K, 1995, INDIAN J CHEM B, V34, P944
[4]  
Avasthi K, 1998, INDIAN J CHEM B, V37, P754
[5]   Design and synthesis of pyrazolo[3,4-d]pyrimidine core based dissymmetrical 'Leonard linker' compounds:: 1H NMR and crystallographic evidence for folded conformation due to arene interactions [J].
Avasthi, K ;
Farooq, SM ;
Raghunandan, R ;
Maulik, PR .
JOURNAL OF MOLECULAR STRUCTURE, 2006, 785 (1-3) :106-113
[6]   Fine tuning of folded conformation by change of substituents:: 1H NMR and crystallographic evidence for folded conformation due to arene interactions in pyrazolo[3,4-d]pyrimidine core based 'propylene linker' compounds [J].
Avasthi, K ;
Aswal, S ;
Kumar, R ;
Yadav, U ;
Rawat, DS ;
Maulik, PR .
JOURNAL OF MOLECULAR STRUCTURE, 2005, 750 (1-3) :179-185
[7]   Unusual molecular conformation in dissymmetric propylene-linker compounds containing pyrazolo[3,4-d]pyrimidine and phthalimide moieties [J].
Avasthi, K ;
Bhagat, D ;
Bal, C ;
Sharon, A ;
Yadav, U ;
Maulik, PR .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2003, 59 :O409-O412
[8]   A stacked pyrazolo[3,4-d]pyrimidine-based flexible molecule:: the effect on stacking of a bulky isopropyl group in comparison with a methyl/ethyl group [J].
Avasthi, K ;
Farooq, SM ;
Rawat, DS ;
Sharon, A ;
Maulik, PR .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2003, 59 :O523-O524
[9]   A stacked pyrazolo[3,4-d]pyrimidine-based flexible molecule:: the effect of a bulky benzyl group on intermolecular stacking in comparison with methyl and ethyl groups [J].
Avasthi, K ;
Tewari, A ;
Rawat, DS ;
Sharon, A ;
Maulik, PR .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2002, 58 (08) :o494-o495
[10]   A stacked pyrazolo[3,4-d]pyrimidine-based flexible molecule:: the effect on stacking of an ethyl group in comparison with a methyl group [J].
Avasthi, K ;
Aswal, S ;
Maulik, PR .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2001, 57 (11) :1324-1325