Abstract
The reaction of benzyl chloride with tetramethylethylenediamine (tmen) results in the formation of the quaternary diammonium dichloride trihydrate (dbtmen)Cl2·3H2O 1 (dbtmen is N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium) in good yields. 1 crystallises in the monoclinic P21/c space group and its structure consists of N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium dication, two chloride anions and three crystal water molecules all of which are located in general positions. The organic dication is H-bonded to the chloride anions and the crystal waters with the help of intra-and intermolecular C-H···Cl and C-H···O interactions, while the chloride anions are linked to the crystal waters via O-H···Cl interactions. One of the crystal waters is linked through an intermolecular O-H···O bond with another water resulting in the formation of a water dimer. The O-H···Cl and O-H···O interactions between the chloride anions and water molecules lead to the formation of a five-membered {O3Cl2} cyclic dichloride containing a water dimer. The five-membered rings are linked into a chain with the aid of a O-H···Cl interaction. The organic cations are organised in zigzag fashion on either side of the chain and are further linked to the anionic water chain via weak C-H···O and C-H···Cl interactions, leading to the supramolecular organisation of the rings into a spiral-like of chain.
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References
Jayaraman K, Chaudhary A and Rao C N R 2002 Solid State Sci. 4 413
Raghavaiah P, Supriya S and Das S K 2005 Cryst. Eng. Commun. 7 167
Raghavaiah P, Supriya S and Das S K 2006 Chem. Commun. 2762
Ludwig R 2001 Angew. Chem. Int. Ed. 40 1808
Infantes L and Motherwell S 2002 Cryst. Eng. Commun. 4 454
Infantes L, Chisolm J and Motherwell S 2003 Cryst. Eng. Commun. 5 480
Mascal M, Infantes L and Chisolm J 2006 Angew. Chem. Int. Ed. 45 32
Liu K, Cruzan J D and Saykally R J 1996 Science 271 929
Maheswari S, Patel N, Sathyamurthy N, Kulkarni A D and Gadre S R 2001 J. Phys. Chem. 105 10525
Keutsch F N, Cruzan J D and Saykally R J 2003 Chem. Rev. 103 2533
Chacko K K and Saenger W 1981 J. Am. Chem. Soc. 1037 1708
Supriya S, Manikumari S, Raghavaiah P and Das S K 2003 New J. Chem. 27 218
Srinivasan B R, Sawant J V, Näther C and Bensch W (unpublished results)
Long L S, Wu Y R, Huang R B and Zheng L S 2004 Inorg. Chem. 43 3798
Ghosh S K and Bharadwaj P K 2004 Inorg. Chem. 43 5180
Doedens R J, Yohannes E and Khan M I 2002 Chem. Commun. 62
Prasad T K and Rajasekharan M V 2006 Cryst. Growth Design 6 488
Atwood J L, Barbour L J, Ness T J, Raston C L and Raston P L 2001 J. Am. Chem. Soc. 123 7192
Neogi S, Savitha G and Bharadwaj P K 2004 Inorg. Chem. 43 3771
Ma B Q, Sun H L and Gao S 2004 Angew. Chem. Int. Ed. 43
Ghosh S K and Bharadwaj P K 2004 Angew. Chem. Int. Ed. 43
Ghosh S K and Bharadwaj P K 2004 Inorg. Chem. 43 6887
Raghuraman K, Katti K K, Barbour L J, Pillarsetty N, Barnes C L and Katti K V 2003 J. Am. Chem. Soc. 125 6955
Lakshminarayanan P S, Suresh E and Ghosh P 2005 J. Am. Chem. Soc. 127 13132
Chand D K and Bharadwaj P K 1998 Inorg. Chem. 37 5050
Sujit K G and Bharadwaj P K 2003 Inorg. Chem. 42 8250
Manikumari S, Shivaiah V and Das S K 2002 Inorg. Chem. 41 6953
Dyke T R, Mack K M and Muenter J S 1977 J. Chem. Phys. 66 498
Odutola J A and Dyke T R 1980 J. Chem. Phys. 72 5062
Vernon M F, Krajnovich D J, Kwok H S, Lisy J M, Shen Y R and Lee Y T 1982 J. Chem. Phys. 77 47
Srinivasan B R, Dhuri S N, Näther C and Bensch W 2005 Inorg. Chim. Acta 358 279
Srinivasan B R, Näther C and Bensch W 2006 Acta Crystallogr. C62 m98
Srinivasan B R, Näther C and Bensch W 2005 Acta Crystallogr. E61 m2454; Srinivasan B R, Nather C Naik A R and Bensch W 2006 Acta Crystallogr. E62 m1635
Srinivasan B R, Dhuri S N, Poisot M, Näther C and Bensch W 2005 Z. Anorg. Allg. Chem. 631 1087
Srinivasan B R, Näther C, Dhuri S N and Bensch W 2006 Monats. Chem. 137 397
Srinivasan B R, Näther C, Dhuri S N and Bensch W 2006 Polyhedron 25 3269
Sheldrick G M 1997 SHELXS-97 and SHELXL-97: Programs for crystal structure solution and refinement, University of Gottingen, Germany
Srinivasan B R, Dhuri S N, Sawant J V, Näther C and Bensch W 2006 J. Chem. Sci. 118 211
Kabak M, Elerman Y, Ünaleroglu C, Mert Y and Durlu T N 2000 Acta Crystallogr. C56 e66
Annan T A, Chadha R K and Tuck D G 1991 Acta Crystallogr. C47 151
Bondi A 1964 J. Phys. Chem. 68 441
Desiraju G R and Steiner T 1999 The weak hydrogen bond in structural chemistry and biology (Oxford: University Press)
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Dedicated to Prof. Sabyasachi Sarkar on the occasion of his 60th birthday
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Srinivasan, B.R., Mhalsikar, R.G., Rane, K.S. et al. A spiral-like chain from a hydrogen-bonded cyclic dichloride containing a water dimer in a quaternary diammonium dichloride trihydrate. J Chem Sci 119, 21–27 (2007). https://doi.org/10.1007/s12039-007-0004-x
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DOI: https://doi.org/10.1007/s12039-007-0004-x