Supramolecular signatures of adenine-containing organostannoxane assemblies

Vadapalli Chandrasekhar; Subrata Kundu; Jitendra Kumar; Sandeep Verma; Kandasamy Gopal; Amaresh Chaturbedi; Kuppuswamy Subramaniam

doi:10.1021/cg3018776

Supramolecular signatures of adenine-containing organostannoxane assemblies

Vadapalli Chandrasekhar, Subrata Kundu, Jitendra Kumar, Sandeep Verma, Kandasamy Gopal, Amaresh Chaturbedi, Kuppuswamy Subramaniam

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

The reactions of 3-(N9-adeninyl) propanoic acid (LH) with various di- and triorganotin oxides have been investigated. Thus, the reaction of di-tert-butyltin oxide (t-Bu₂SnO)₃ in a 3:1 ratio afforded the dinuclear derivative [t-Bu₂Sn(μ-OH)L]₂· 7H₂O (1). A similar reaction involving bis(tri-n-butyltin)oxide, (n-Bu₃Sn)₂O, in a 2:1 ratio afforded the one-dimensional (1D) coordination polymer [n-Bu₃SnL·0.33H₂O] _n (2). Similarly the reaction with (n-Bu₂SnO)_n in a 2:1 ratio afforded the tetranuclear [{n-Bu₂Sn} ₂(μ₃-O)(μ-OH)L]₂ (3). On the other hand, a similar reaction in a 1:1 ratio also gave the tetranuclear product [{n-Bu ₂Sn}₂(μ₃-O)L₂]₂ (4). The molecular structure of 1reveals a central dinuclear Sn₂O ₂ motif where the two tin centers are bridged by two μ-OH groups. Each tin is bound with a monodentate carboxylate group; the Cî - O unit of these carboxylates is involved in an intramolecular hydrogen bonding with the bridging OH unit. The supramolecular structure of 1 reveals the formation of a 1D zigzag chain mediated by intermolecular hydrogen bonding interaction through the Watson-Crick or the Hoogsteen faces. 2 is a 1D coordination polymer formed by the successive bridging of triorganotin units by the carboxylate ligand L. The supramolecular structure of 2 reveals that two 1D coordination polymers interact to generate novel adenine homotrimers formed as a result of alternating Watson-Crick-Watson-Crick and Hoogsteen-Watson-Crick interactions. The molecular structures of 3 and 4 reveal them to be tetranuclear possessing a ladder-like structure. The essential difference between their molecular structures is that in 4 there are four carboxylate ligands, while in 3 there are only two. Both of these complexes reveal intramolecular and intermolecular hydrogen bonding and π···π stacking interactions. The nematicidal activity of 1-3 was examined against Caenorhabditis elegans. Compound 2 was found to be highly active, effecting a high mortality even at very low concentrations such as 25 or 10 ppm.

Original language	English
Pages (from-to)	1665-1675
Number of pages	11
Journal	Crystal Growth and Design
Volume	13
Issue number	4
DOIs	https://doi.org/10.1021/cg3018776
State	Published - 3 Apr 2013
Externally published	Yes

ASJC Scopus subject areas

Chemistry (all)
Materials Science (all)
Condensed Matter Physics

Access to Document

10.1021/cg3018776

Cite this

@article{a57f6ac4416d4274ac63fec66b3bc3a4,

title = "Supramolecular signatures of adenine-containing organostannoxane assemblies",

abstract = "The reactions of 3-(N9-adeninyl) propanoic acid (LH) with various di- and triorganotin oxides have been investigated. Thus, the reaction of di-tert-butyltin oxide (t-Bu2SnO)3 in a 3:1 ratio afforded the dinuclear derivative [t-Bu2Sn(μ-OH)L]2· 7H2O (1). A similar reaction involving bis(tri-n-butyltin)oxide, (n-Bu3Sn)2O, in a 2:1 ratio afforded the one-dimensional (1D) coordination polymer [n-Bu3SnL·0.33H2O] n (2). Similarly the reaction with (n-Bu2SnO)n in a 2:1 ratio afforded the tetranuclear [{n-Bu2Sn} 2(μ3-O)(μ-OH)L]2 (3). On the other hand, a similar reaction in a 1:1 ratio also gave the tetranuclear product [{n-Bu 2Sn}2(μ3-O)L2]2 (4). The molecular structure of 1reveals a central dinuclear Sn2O 2 motif where the two tin centers are bridged by two μ-OH groups. Each tin is bound with a monodentate carboxylate group; the C{\^i} - O unit of these carboxylates is involved in an intramolecular hydrogen bonding with the bridging OH unit. The supramolecular structure of 1 reveals the formation of a 1D zigzag chain mediated by intermolecular hydrogen bonding interaction through the Watson-Crick or the Hoogsteen faces. 2 is a 1D coordination polymer formed by the successive bridging of triorganotin units by the carboxylate ligand L. The supramolecular structure of 2 reveals that two 1D coordination polymers interact to generate novel adenine homotrimers formed as a result of alternating Watson-Crick-Watson-Crick and Hoogsteen-Watson-Crick interactions. The molecular structures of 3 and 4 reveal them to be tetranuclear possessing a ladder-like structure. The essential difference between their molecular structures is that in 4 there are four carboxylate ligands, while in 3 there are only two. Both of these complexes reveal intramolecular and intermolecular hydrogen bonding and π···π stacking interactions. The nematicidal activity of 1-3 was examined against Caenorhabditis elegans. Compound 2 was found to be highly active, effecting a high mortality even at very low concentrations such as 25 or 10 ppm.",

author = "Vadapalli Chandrasekhar and Subrata Kundu and Jitendra Kumar and Sandeep Verma and Kandasamy Gopal and Amaresh Chaturbedi and Kuppuswamy Subramaniam",

year = "2013",

month = apr,

day = "3",

doi = "10.1021/cg3018776",

language = "English",

volume = "13",

pages = "1665--1675",

journal = "Crystal Growth and Design",

issn = "1528-7483",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - Supramolecular signatures of adenine-containing organostannoxane assemblies

AU - Chandrasekhar, Vadapalli

AU - Kundu, Subrata

AU - Kumar, Jitendra

AU - Verma, Sandeep

AU - Gopal, Kandasamy

AU - Chaturbedi, Amaresh

AU - Subramaniam, Kuppuswamy

PY - 2013/4/3

Y1 - 2013/4/3

N2 - The reactions of 3-(N9-adeninyl) propanoic acid (LH) with various di- and triorganotin oxides have been investigated. Thus, the reaction of di-tert-butyltin oxide (t-Bu2SnO)3 in a 3:1 ratio afforded the dinuclear derivative [t-Bu2Sn(μ-OH)L]2· 7H2O (1). A similar reaction involving bis(tri-n-butyltin)oxide, (n-Bu3Sn)2O, in a 2:1 ratio afforded the one-dimensional (1D) coordination polymer [n-Bu3SnL·0.33H2O] n (2). Similarly the reaction with (n-Bu2SnO)n in a 2:1 ratio afforded the tetranuclear [{n-Bu2Sn} 2(μ3-O)(μ-OH)L]2 (3). On the other hand, a similar reaction in a 1:1 ratio also gave the tetranuclear product [{n-Bu 2Sn}2(μ3-O)L2]2 (4). The molecular structure of 1reveals a central dinuclear Sn2O 2 motif where the two tin centers are bridged by two μ-OH groups. Each tin is bound with a monodentate carboxylate group; the Cî - O unit of these carboxylates is involved in an intramolecular hydrogen bonding with the bridging OH unit. The supramolecular structure of 1 reveals the formation of a 1D zigzag chain mediated by intermolecular hydrogen bonding interaction through the Watson-Crick or the Hoogsteen faces. 2 is a 1D coordination polymer formed by the successive bridging of triorganotin units by the carboxylate ligand L. The supramolecular structure of 2 reveals that two 1D coordination polymers interact to generate novel adenine homotrimers formed as a result of alternating Watson-Crick-Watson-Crick and Hoogsteen-Watson-Crick interactions. The molecular structures of 3 and 4 reveal them to be tetranuclear possessing a ladder-like structure. The essential difference between their molecular structures is that in 4 there are four carboxylate ligands, while in 3 there are only two. Both of these complexes reveal intramolecular and intermolecular hydrogen bonding and π···π stacking interactions. The nematicidal activity of 1-3 was examined against Caenorhabditis elegans. Compound 2 was found to be highly active, effecting a high mortality even at very low concentrations such as 25 or 10 ppm.

AB - The reactions of 3-(N9-adeninyl) propanoic acid (LH) with various di- and triorganotin oxides have been investigated. Thus, the reaction of di-tert-butyltin oxide (t-Bu2SnO)3 in a 3:1 ratio afforded the dinuclear derivative [t-Bu2Sn(μ-OH)L]2· 7H2O (1). A similar reaction involving bis(tri-n-butyltin)oxide, (n-Bu3Sn)2O, in a 2:1 ratio afforded the one-dimensional (1D) coordination polymer [n-Bu3SnL·0.33H2O] n (2). Similarly the reaction with (n-Bu2SnO)n in a 2:1 ratio afforded the tetranuclear [{n-Bu2Sn} 2(μ3-O)(μ-OH)L]2 (3). On the other hand, a similar reaction in a 1:1 ratio also gave the tetranuclear product [{n-Bu 2Sn}2(μ3-O)L2]2 (4). The molecular structure of 1reveals a central dinuclear Sn2O 2 motif where the two tin centers are bridged by two μ-OH groups. Each tin is bound with a monodentate carboxylate group; the Cî - O unit of these carboxylates is involved in an intramolecular hydrogen bonding with the bridging OH unit. The supramolecular structure of 1 reveals the formation of a 1D zigzag chain mediated by intermolecular hydrogen bonding interaction through the Watson-Crick or the Hoogsteen faces. 2 is a 1D coordination polymer formed by the successive bridging of triorganotin units by the carboxylate ligand L. The supramolecular structure of 2 reveals that two 1D coordination polymers interact to generate novel adenine homotrimers formed as a result of alternating Watson-Crick-Watson-Crick and Hoogsteen-Watson-Crick interactions. The molecular structures of 3 and 4 reveal them to be tetranuclear possessing a ladder-like structure. The essential difference between their molecular structures is that in 4 there are four carboxylate ligands, while in 3 there are only two. Both of these complexes reveal intramolecular and intermolecular hydrogen bonding and π···π stacking interactions. The nematicidal activity of 1-3 was examined against Caenorhabditis elegans. Compound 2 was found to be highly active, effecting a high mortality even at very low concentrations such as 25 or 10 ppm.

UR - http://www.scopus.com/inward/record.url?scp=84875798457&partnerID=8YFLogxK

U2 - 10.1021/cg3018776

DO - 10.1021/cg3018776

M3 - Article

AN - SCOPUS:84875798457

SN - 1528-7483

VL - 13

SP - 1665

EP - 1675

JO - Crystal Growth and Design

JF - Crystal Growth and Design

IS - 4

ER -

Supramolecular signatures of adenine-containing organostannoxane assemblies

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this