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Comparison of sp-C–H···N Hydrogen Bond Lengths in Fluorinated and Nonfluorinated Ethynylbenzenes

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Abstract

1,4-Diethynyltetrafluorobenzene was prepared and separately co-crystalized with 4,4′-bipyridine, 1,2-bis(4′-pyridyl)ethyne and trans-1,2-bis(4′-pyridyl)ethane to form 1:1 co-crystals that each contain essentially linear C–H···N hydrogen bonded ribbons of alternating diyne and dipyridine. The C–H···N hydrogen bond distances and angles in the 1:1 co-crystals are analyzed and compared to the previously reported C–H···N hydrogen bond distances and angles in the corresponding co-crystals formed with 1,4-diethynylbenzene.

Graphical Abstract

1,4-Diethynyltetrafluorobenzene was prepared and separately co-crystalized with 4,4′-bipyridine, 1,2-bis(4′-pyridyl)ethyne and trans-1,2-bis(4′-pyridyl)ethane to form 1:1 co-crystals that each contain essentially linear C–H···N hydrogen bonded ribbons of alternating diyne and dipyridine. The C–H···N hydrogen bond distances and angles in the 1:1 co-crystals are analyzed and compared to the previously reported C–H···N hydrogen bond distances and angles in the corresponding co-crystals formed with 1,4-diethynylbenzene.

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References

  1. Desiraju GR, Steiner T (1999) The weak hydrogen bond in structural chemistry and biology. Oxford University Press, Oxford

    Google Scholar 

  2. Bosch E (2010) Cryst Growth Des 10:3808–3813

    Article  CAS  Google Scholar 

  3. Neenan B, Thomas X, Whitesides GM (1988) J Org Chem 53:2489–2496

    Article  CAS  Google Scholar 

  4. ApexII Suite (2006) Bruker AXS Ltd., Madison

  5. Sheldrick GM (2008) Acta Crystallogr A 64:112

    Article  CAS  Google Scholar 

  6. Barbour L, Atwood JA (2003) Cryst Growth Des 3:3

    Article  Google Scholar 

  7. Prasang C, Whitwood AC, Bruce DW (2009) Cryst Growth Des 9:5319

    Article  CAS  Google Scholar 

  8. Walsh RB, Padgett CW, Metrangolo P, Resnati G, Hanks TW, Pennington WT (2001) Cryst Growth Des 1:165

    Article  CAS  Google Scholar 

  9. Hehre WJ, Ohlinger WS (2010) Spartan’10 tutorial and user’s guide. Wavefunction, Inc., Irvine

    Google Scholar 

Download references

Acknowledgment

The Missouri State University Provost Incentive Fund funded the purchase of the X-ray diffractometer.

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  1. Chemistry Department, Missouri State University, 901 South National Avenue, Springfield, MO, 65897, USA

    Eric Bosch

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  1. Eric Bosch
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Correspondence to Eric Bosch.

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Bosch, E. Comparison of sp-C–H···N Hydrogen Bond Lengths in Fluorinated and Nonfluorinated Ethynylbenzenes. J Chem Crystallogr 44, 287–292 (2014). https://doi.org/10.1007/s10870-014-0510-x

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  • DOI: https://doi.org/10.1007/s10870-014-0510-x

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