Abstract
New phosphoric triamides 1–9 were synthesized by the reaction of N-2,4-dichlorobenzoyl phosphoramidic dichloride with various cyclic aliphatic amines and the products were characterized by 1H, 13C, 31P NMR, IR spectroscopy and elemental analysis. Surprisingly, the 1H NMR spectrum of 2 indicated long range 6 J (P, H) coupling constant = 1.3, 1.4 Hz and those of molecules 3, 4, 6–8 display long-range 4 J (H, H) coupling constants (1.8–1.9 Hz) for the coupling of aromatic protons in 2,4-dichlorophenyl rings. 1H NMR spectra indicated 3 J (PNCH) for enantiotopic and diastereotopic benzylic CH2 protons in compounds 7 and 8. The spectroscopic data of newly synthesized compounds were compared with those related N-benzoyl derivatives. The structures of compounds 5, 8 and 10 (2,4-Cl2-C6H3C(O)NHP(O)[NCH2CH(CH3)2]2) have been determined by X-ray crystallography. The structures form centrosymmetric dimers through intermolecular strong -P=O…H-N-hydrogen bonds. The dimers connect to each other via rather strong and weak C-H…O plus weak C-H…Cl H-bonds to produce a 1-D network for 5 while 3-D polymeric chains for 8 and 10.
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Jianga Y and Hu L 2007 Bioorg. Med. Chem. Lett. 17 517
Li Z, Han J, Jiang Y, Browne P, Knox R J and Hu L 2003 Bioinorg. Med. Chem. 11 4171
Jiang Y and Hu L 2008 Bioorg. Med. Chem. Lett. 18 4059
Dewine K G, McGuigan C, O’Cunnor T J, Nicholis S R and Kinchington D 1990 AIDS 4 371
Jiang Y, DiPaola R S and Hu L 2009 Bioorg. Med. Chem. Lett. 19 2587
Zou X J, Jin G Y and Zhang Z X 2002 J. Agricult. Food Chem. 50 1451
Akgür S A, Öztürk P, Solak I, Moral A R and Ege B 2003 Forensic Sci. Int. 133 136
Berlicki L and Kafarski P 2002 Pestic. Biochem. Phys. 73 94
Pardio V T, Ibarra N and Rodriguez M A 2001 J. Agricult. Food Chem. 49 6057
Denmark S E and Fu J 2003 J. Am. Chem. Soc. 125 2208
Gubina K E, Shatrava J A, Amirkhanov V A, Ovchynnikov V A and Amirkhanov V M 2000 Polyhedron 19 2203
Silvestru C, Rösler R, Silvestru A and Drake J E 2002 J. Organomet. Chem. 642 71
Gholivand K and Shariatinia Z 2006 J. Organomet. Chem. 691 4215
Tecilla P, Chang S-K and Hamilton A D 1990 J. Am. Chem. Soc. 112 9586
Moreno G E, Quintero L, Bernés S and de Parrodi C A 2004 Tetrahedron Lett. 45 4245
Timperley C M, Bird M and Waters M J 2005 J. Fluorine Chem. 126 892
Timperley C M and Waters M 2005 J. Fluorine Chem. 126 1144
Anagnostis J and Turnbull M M 2004 Polyhedron 23 125
Domínguez Z J, Cortez M T and Gordillo B 2001 Tetrahedron 57 9799
Necas M, Foreman M R St J, Dastych D and Novosad J 2001 Inorg. Chem. Commun. 4 36
Gubina K E and Amirkhanov V M 2000 Z. Naturforsch. 55b 1015
Gubina K E, Ovchynnikov V A, Amirkhanov V M, Silva T Y, Skopenko V V, Glowiak T and Kozlowski H 1999 Z. Naturforsch. 54b 1357
Amirkhanov V M, Ovchynnikov V A, Glowiak T and Kozlowski H 1997 Z. Naturforsch. 52b 1331
Gholivand K, Mostaanzadeh H, Shariatinia Z and Oroujzadeh N 2006 Main Group Chem. 5 95
Gholivand K, Pourayoubi M, Shariatinia Z and Mostaanzadeh H 2005 Polyhedron 24 655
Narula P M, Day C S, Powers B A, Odian M A, Lachgar A, Pennington W T and Noftle R E 1999 Polyhedron 18 1751
Chivers T, Krahn M, Schatte G and Parvez M 2003 Inorg. Chem. 42 3994
Gholivand K, Shariatinia Z, Mashhadi S M, Daeepour F, Farshidnasab N, Mahzouni H R, Taheri N, Amiri S and Ansar S 2009 Polyhedron 28 307
Gholivand K, Vedova C O D, Erben M F, Mahzouni H R, Shariatinia Z and Amiri S 2008 J. Mol. Struct. 874 178
Gholivand K, Shariatinia Z, Afshar F, Faramarzpour H and Yaghmaian F 2007 Main Group Chem. 6 231
Gholivand K and Shariatinia Z 2007 Struct. Chem. 18 95
Font M, Domínguez M-J, Sanmartín C, Palop J A, San-Francisco S, Urrutia O, Houdusse F and García-Mina J M 2008 J. Agric. Food Chem. 56 8451
Domínguez M-J, Sanmartín C, Font M, Palop J A, San-Francisco S, Urrutia O, Houdusse F and García-Mina J M 2008 J. Agric. Food Chem. 56 3721
Vassiliou S, Grabowiecka A, Kosikowska P, Yiotakis A, Kafarski P and Berlicki Ł 2008 J. Med. Chem. 51 5736
Siddiqui A Q, Ballatore C, McGuigan C, Clercq E D and Balzarini J 1999 J. Med. Chem. 42 393
Chandrasekaran A, Sood P, Day R O and Holmes R R 1999 Inorg. Chem. 38 3952
Davis A M and Teague S J 1999 Angew. Chem., Int. Ed. Engl. 38 736
Derewenda Z S, Lee L and Derewenda U 1995 J. Mol. Biol. 252 248
Swamy K C K, Kumaraswamy S and Kommana P 2001 J. Am. Chem. Soc. 123 12642
Kumar K V P P and Swamy K C K 2005 Acta Cryst. C61 o668
Muthiah C and Swamy K C K 1999 Acta Cryst. C55 110
Muthiah C, Said M A, Pulm M, Herbst-Irmer R and Swamy K C K 2000 Polyhedron 19 63
Gholivand K and Oroujzadeh N 2008 Main Group Chem. 7 251
Stoe and Cie, X-RED, version 1.28b: Program for data reduction and absorption correction, Stoe and Cie GmbH: Darmatadt, Germany, 2005
Bruker, SMART. Bruker Molecular Analysis Research Tool, v. 5.059. Bruker AXS, Madison, Wisconsin, USA, 1998
Sheldrick G M, SHELX 97, University of Gottingen, Germany, 1997
Sheldrick G M, SHELXTL v. 5.10, Structure Determination Software Suit, Bruker AXS, Madison, WI, USA, 1998
Barfield M and Chakrabarti B 1969 Chem. Rev. 69 757
Corbridge D E C 1995 Phosphorus, an outline of its chemistry, biochemistry and technology (The Netherlands: Elsevier), 5th edn
Gilheany D G 1994 Chem. Rev. 94 1339
Gholivand K, Mojahed F, Madani A A and Bijanzadeh H R 2006 Z. Anorg. Allg. Chem. 632 1570
Gholivand K and Pourayoubi M 2004 Z. Anorg. Allg. Chem. 630 1330
Gholivand K, Shariatinia Z and Pourayoubi M 2005 Z. Anorg. Allg. Chem. 631 961
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Gholivand, K., Oroujzadeh, N. & Shariatinia, Z. N-2,4-dichlorobenzoyl phosphoric triamides: Synthesis, spectroscopic and X-ray crystallography studies. J Chem Sci 122, 549–559 (2010). https://doi.org/10.1007/s12039-010-0089-5
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DOI: https://doi.org/10.1007/s12039-010-0089-5