Crystal and Molecular Structure of 3-Iodo-2-propynyl-N-butylcarbamate

Avtomonov, Evgeni V.; Grüning, Rainer; Lorberth, Jörg

doi:10.1515/znb-1997-0220

Cited by 2 publications

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References 3 publications

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“…The crystal structure of the pure IPBC reveals the pivotal role of the carbamate and iodoalkyne groups in the organization of the molecules in the crystal lattice. The carbonyl oxygen acts as a bidentate electron-donor site and forms one H-bond with the N–H moiety (O···N distance 2.904(6) Å, C–O···N angle 140.9(3)°) and one XB with the C–I moiety (C–I···O distance 2.933(4) Å, C–I···O angle 175.4(2)°) (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Halogen Bonding and Pharmaceutical Cocrystals: The Case of a Widely Used Preservative

et al. 2013

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3-Iodo-2-propynyl-N-butylcarbamate (IPBC) is an iodinated antimicrobial product used globally as a preservative, fungicide, and algaecide. IPBC is difficult to obtain in pure form as well as to handle in industrial products because it tends to be sticky and clumpy. Here, we describe the preparation of four pharmaceutical cocrystals involving IPBC. The obtained cocrystals have been characterized by X-ray diffraction, solution and solid-state NMR, IR, and DSC analyses. In all the described cases the halogen bond (XB) is the key interaction responsible for the self-assembly of the pharmaceutical cocrystals thanks to the involvement of the 1-iodoalkyne moiety of IPBC, which functions as a very reliable XB-donor, with both neutral and anionic XB-acceptors. Most of the obtained cocrystals have improved properties with respect to the source API, in terms, e.g., of thermal stability. The cocrystal involving the GRAS excipient CaCl2 has superior powder flow characteristics compared to the pure IPBC, representing a promising solution to the handling issues related to the manufacturing of products containing IPBC.

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Section: Resultsmentioning

confidence: 99%

Halogen Bonding and Pharmaceutical Cocrystals: The Case of a Widely Used Preservative

et al. 2013

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Diiodoacetylene: compact, strong ditopic halogen bond donor

et al. 2012

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Diiodoacetylene, C 2 I 2 , is the smallest ditopic halogen bond donor other than I 2 or other dihalogens. A convenient synthesis of diiodoacetylene from the common Sonagashira coupling reagent Me 3 SiChCH, is described. The halogen-bonded adducts of C 2 I 2 with dimethylformamide (DMF), pyrazine (pyz) and 1,4-diazabicyclooctane (dabco) have been characterised by X-ray crystallography. All adopt 1D halogen-bonded chains linked via short C-I/O [I/O 2.834(4)-2.888(4) A; C-I/O > 170 ] or C-I/N [I/N 2.715(3)-2.832(7) A; C-I/N > 175 ] interactions. Attempts to synthesise the adduct of C 2 I 2 with hexamethylenetetramine (hmta) resulted in isolation and crystallographic characterisation of the adduct of C 2 I 4 $hmta, indicating decomposition of C 2 I 2 to yield C 2 I 4 in solution. The adduct comprises two independent C 2 I 4 molecules that act, respectively, as tetratopic and ditopic halogen bond donors forming C-I/N interactions [I/N 2.948(7)-2.999(8) A; C-I/N > 165 ], occupying three of the four nitrogen sites on htma. The remaining nitrogen sites engage in N/C(p) interactions directed orthogonal to the plane of the ditopic C 2 I 4 molecules. Separate surveys of halogen bonds formed by diiodo(poly)alkynes I(ChC) n I (n ¼ 1-3) and by C 2 I 4 molecules indicate that C-I/N halogen bonds are shorter, when normalised for van der Waals radii, and, by inference, stronger than halogen bonds involving other acceptor groups, and demonstrates that C sp -I/N halogen bonds are generally shorter C sp 2-I/N halogen bonds.

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Crystal and Molecular Structure of 3-Iodo-2-propynyl-N-butylcarbamate

Cited by 2 publications

References 3 publications

Halogen Bonding and Pharmaceutical Cocrystals: The Case of a Widely Used Preservative

Halogen Bonding and Pharmaceutical Cocrystals: The Case of a Widely Used Preservative

Diiodoacetylene: compact, strong ditopic halogen bond donor

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