Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH FRONT

Application of the Variable Oxygen Probe to Determine the π-Electron Donor Ability of the Alkyne Group

Benjamin L. Harris A and Jonathan M. White A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry and the BIO-21 Institute, The University of Melbourne, Parkville, Vic. 3010, Australia.

B Corresponding author. Email: whitejm@unimelb.edu.au

Australian Journal of Chemistry 67(12) 1866-1870 https://doi.org/10.1071/CH14395
Submitted: 18 June 2014  Accepted: 31 July 2014   Published: 18 September 2014

Abstract

Eight ester and ether derivatives of propargyl alcohol with varying electron demand were structurally characterised using low temperature X-ray crystallography, these were combined with seven derivatives obtained from the Cambridge Structural Database. Variable oxygen probe analysis of these derivatives provided evidence that the ethynyl substituent is a relatively weak π-electron donor, and is a slightly less effective donor than the C–C bond of an ethyl substituent.


References

[1]  A. J. Briggs, R. Glenn, P. G. Jones, A. J. Kirby, P. Ramaswamy, J. Am. Chem. Soc. 1984, 106, 6200.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXlslShtr8%3D&md5=53f8a34f5a589478eb100b80a94eca9bCAS |

[2]  R. D. Amos, N. C. Handy, P. G. Jones, A. J. Kirby, J. K. Parker, J. M. Percy, M. D. Su, J. Chem. Soc., Perkin Trans. 2 1992, 549.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38XisFCqtr4%3D&md5=40ba6acf3ec7a83c63a063762c5da7b9CAS |

[3]  M. Spiniello, J. M. White, Org. Biomol. Chem. 2003, 1, 3094.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXms12gsL0%3D&md5=801c927c79787e65ac71ffa8de8a3cd9CAS | 14518133PubMed |

[4]  A. J. Green, J. Giordano, J. M. White, Aust. J. Chem. 2000, 53, 285.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXlsl2mtbg%3D&md5=990a78af342bb67cd957ef617d057a1bCAS |

[5]  J. M. White, J. B. Lambert, M. Spiniello, S. A. Jones, R. W. Gable, Chem. – Eur. J. 2002, 8, 2799.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XltVGrtrY%3D&md5=52da3eaf6a5fdaa8cb94a9e582d7793eCAS | 12391659PubMed |

[6]  B. R. Pool, J. M. White, P. P. Wolynec, J. Org. Chem. 2000, 65, 7595.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXntVWhsbg%3D&md5=fadcf03e3cf36b349988129d04b2d82eCAS | 11076620PubMed |

[7]  W. Jackson, J. M. White, Aust. J. Chem. 2008, 61, 956.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsVyku7rF&md5=1511f4617104bf72d5313d11219eaf7aCAS |

[8]  N. L. Fifer, J. M. White, Org. Biomol. Chem. 2005, 3, 1776.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXjslGqur8%3D&md5=588f0f6a71e068f1bbff8bfc79d85b71CAS | 15858663PubMed |

[9]  S. D. Yeoh, C. E. Skene, J. M. White, J. Org. Chem. 2013, 78, 311.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhvVSqt7%2FE&md5=32b6ffac19f0f053b4073d5536fde42dCAS | 23215360PubMed |

[10]  B. L. Harris, G. P. Savage, J. M. White, Org. Biomol. Chem. 2013, 11, 3151.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXmtlCgtL8%3D&md5=6c2023f34a2b7dcac7b4af72b740d0b5CAS |

[11]  (a) S. Swaminathan, K. V. Narayanan, Chem. Rev. 1971, 71, 429.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3MXlsFWnsbk%3D&md5=3070dae0c226a50f9922c222cc9c9132CAS |
      (b) S. M. Lukyanov, A. V. Koblik, L. A. Muradyan, Russ. Chem. Rev. 1998, 67, 817.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  T. T. Tidwell, Angew. Chem. 1984, 96, 16.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXhsFKju74%3D&md5=db521ea3ae6b1e69ad941044db86e73fCAS |

[13]  F. H. Allen, Acta Crystallogr., Sect. B: Struct. Sci., Cryst. Eng. Mater. 2002, B58, 380.
         | 1:CAS:528:DC%2BD38XktVOqu74%3D&md5=e404896cf797fe7e68bda46aed1f6279CAS |

[14]     (a) D. R. Lide, CRC Handbook of Chemistry and Physics, 79th edn 1998 (CRC Press: Boca Raton, FL).
         (b) J. F. King, Sulphonic Acids, Esters and their Derivatives 1991, Ch. 6, pp. 249–259 (John Wiley & Sons: New York, NY).
         (c) D. D. Perrin, Dissociation Constants of Organic Bases in Aqueous Solution: Supplement 1972 (Butterworths: London).
         (d) E. P. Serjeant, B. Dempsey, Ionization Constants of Organic Acids in Aqueous Solution 1979 (Pergamon: Oxford).
      (e) A. Habbi-Yangjeh, M. Danandeh-Jenagharad, M. Nooshar, Bull. Korean Chem. Soc. 2005, 26, 2007.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  J. T. Mague, W. L. Alworth, M. Foroozesh, Acta Crystallogr., Sect. E: Struct. Rep. Online 2001, 57, o220.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXhs1Oltrc%3D&md5=3edaf709679fb40708a4ad456918eeb3CAS |

[16]  E. C. Constable, C. E. Houseworth, N. Neuburger, S. Schaffner, E. J. Shardlow, Inorg. Chim. Acta 2007, 360, 4069.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtlWntLvO&md5=4f36a5de4cd6c08546d648bc37d78176CAS |

[17]  K. Shah, M. Raza, S. W. Shah, Ng, Acta Crystallogr., Sect. E: Struct. Rep. Online 2010, 66, o1939.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXps1agsL4%3D&md5=3e17e5d08dad9fe88e077e0e70e7897eCAS |

[18]  Y. H. Belay, H. H. Kinfe, A. Muller, Acta Crystallogr., Sect. E: Struct. Rep. Online 2012, 68, o3072.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhslKns7vM&md5=17ac477bd16082f0ad42f616de104312CAS |

[19]  S. V. Lindeman, R. A. Dvorikova, I. R. Gol’ding, Y. T. Struchkov, M. M. Teplyakov, Izv. Akad. Nauk. SSSR, Ser. Khim. (Russ. Chem. Bull.) 1993, 1601.
         | 1:CAS:528:DyaK28XjvFGksrw%3D&md5=b048f0faa9b6f62e4d57f81479e9c6aaCAS |

[20]  X.-H. Chang, Acta Crystallogr., Sect. E: Struct. Rep. Online 2006, 62, o5102.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtFOis73P&md5=cfe2b98601510ca9466e4c0dc9ad9b6bCAS |

[21]  I. Doi, T. Okuno, Acta Crystallogr., Sect. E: Struct. Rep. Online 2013, 69, o125.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhsFGksw%3D%3D&md5=71aa4fdb8e9c0272a6f2c1dbb469be20CAS |

[22]  T. A. Albright, J. K. Burdett, W. Whangho, Orbital Interactions in Chemistry 1985 (Wiley: New York, NY).

[23]  S. A. Bateman, D. P. Kelly, R. F. Martin, J. M. White, Aust. J. Chem. 1999, 52, 291.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXktFCju70%3D&md5=bdbc5a71d0a336692df69c274009d0ecCAS |

[24]  Z. V. Belyakova, M. G. Pomerantseva, S. A. Golubov, K. K. Popov, Zh. Obshch. Khim. 1967, 37, 922.
         | 1:CAS:528:DyaF1cXivFOluw%3D%3D&md5=cf1b8cb89b88a65df82705f250bc8d34CAS |

[25]  D. J. Burton, G. A. Hartgraves, J. Hsu, Tetrahedron Lett. 1990, 31, 3699.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXmtlSktr4%3D&md5=327e0871e6c5c0529716c95b5021485cCAS |