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Orthogonal halogen and hydrogen bonds involving a peptide bond model†Electronic supplementary information (ESI) available: Experimental part, DSC, IR spectroscopic and crystallographic data. CCDC 899779-899785. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4ce01514bClick here for additional data file.Click here for additional data file.

Vasylyeva V, Nayak SK, Terraneo G, Cavallo G, Metrangolo P, Resnati G - CrystEngComm (2014)

Bottom Line: The peptide bond model N-methylacetamide self-assembles with a range of dihalotetrafluorobenzenes forming co-crystals that all show the occurrence of orthogonal hydrogen and halogen bonds.

View Article: PubMed Central - PubMed

Affiliation: NFMLab , D.C.M.I.C. "Giulio Natta" , Politecnico di Milano , Via Mancinelli 7 , 20131 Milan , Italy . Email: pierangelo.metrangolo@polimi.it ; Email: giancarlo.terraneo@polimi.it ; ; Tel: (+39) 02 2399 3041.

ABSTRACT

The peptide bond model N-methylacetamide self-assembles with a range of dihalotetrafluorobenzenes forming co-crystals that all show the occurrence of orthogonal hydrogen and halogen bonds.

No MeSH data available.


Synthesis of N-methylacetamide (NMA, 1) co-crystals with various dihalotetrafluorobenzenes (DXTFB, X = Br or I). The orthogonal angle (α) is defined as the angle between XB (C–X···O, X = Br or I) and HB (N–H···O), i.e., ∠X···O···N.
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sch1: Synthesis of N-methylacetamide (NMA, 1) co-crystals with various dihalotetrafluorobenzenes (DXTFB, X = Br or I). The orthogonal angle (α) is defined as the angle between XB (C–X···O, X = Br or I) and HB (N–H···O), i.e., ∠X···O···N.

Mentions: Our goal was to rationally design systems based on the orthogonal HB/XB supramolecular synthon and verify its robustness for use in crystal engineering. For this reason, NMA 1, affording the carbonyl oxygen acceptor site, was co-crystallized with several dihalotetrafluorobenzenes (DXTFBs), the XB donors, 1,2-dibromotetrafluorobenzene (12DBrTFB, 2a), 1,3-dibromotetrafluorobenzene (13DBrTFB, 2b), 1,4-dibromotetrafluorobenzene (14DBrTFB, 2c), 1,2-diiodotetrafluorobenzene (12DITFB, 2d), 1,3-diiodotetrafluorobenzene (13DITFB, 2e), and 1,4-diiodotetrafluorobenzene (14DITFB, 2f). The corresponding complexes 3a–f were obtained (Scheme 1).


Orthogonal halogen and hydrogen bonds involving a peptide bond model†Electronic supplementary information (ESI) available: Experimental part, DSC, IR spectroscopic and crystallographic data. CCDC 899779-899785. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4ce01514bClick here for additional data file.Click here for additional data file.

Vasylyeva V, Nayak SK, Terraneo G, Cavallo G, Metrangolo P, Resnati G - CrystEngComm (2014)

Synthesis of N-methylacetamide (NMA, 1) co-crystals with various dihalotetrafluorobenzenes (DXTFB, X = Br or I). The orthogonal angle (α) is defined as the angle between XB (C–X···O, X = Br or I) and HB (N–H···O), i.e., ∠X···O···N.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4317971&req=5

sch1: Synthesis of N-methylacetamide (NMA, 1) co-crystals with various dihalotetrafluorobenzenes (DXTFB, X = Br or I). The orthogonal angle (α) is defined as the angle between XB (C–X···O, X = Br or I) and HB (N–H···O), i.e., ∠X···O···N.
Mentions: Our goal was to rationally design systems based on the orthogonal HB/XB supramolecular synthon and verify its robustness for use in crystal engineering. For this reason, NMA 1, affording the carbonyl oxygen acceptor site, was co-crystallized with several dihalotetrafluorobenzenes (DXTFBs), the XB donors, 1,2-dibromotetrafluorobenzene (12DBrTFB, 2a), 1,3-dibromotetrafluorobenzene (13DBrTFB, 2b), 1,4-dibromotetrafluorobenzene (14DBrTFB, 2c), 1,2-diiodotetrafluorobenzene (12DITFB, 2d), 1,3-diiodotetrafluorobenzene (13DITFB, 2e), and 1,4-diiodotetrafluorobenzene (14DITFB, 2f). The corresponding complexes 3a–f were obtained (Scheme 1).

Bottom Line: The peptide bond model N-methylacetamide self-assembles with a range of dihalotetrafluorobenzenes forming co-crystals that all show the occurrence of orthogonal hydrogen and halogen bonds.

View Article: PubMed Central - PubMed

Affiliation: NFMLab , D.C.M.I.C. "Giulio Natta" , Politecnico di Milano , Via Mancinelli 7 , 20131 Milan , Italy . Email: pierangelo.metrangolo@polimi.it ; Email: giancarlo.terraneo@polimi.it ; ; Tel: (+39) 02 2399 3041.

ABSTRACT

The peptide bond model N-methylacetamide self-assembles with a range of dihalotetrafluorobenzenes forming co-crystals that all show the occurrence of orthogonal hydrogen and halogen bonds.

No MeSH data available.