Why the Second Bond Exceptionally Effective on pK_a Values of -ynoic (-C≡C-) Compounds? Chemical Education Perspective

R. Sanjeev¹, D. A. Padmavati² and V. Jagannadham^2,

¹Department of Chemistry, Geethanjali College of Engineering and Technology, Cheeryal-501301, Telangana, India

²Department of Chemistry, Osmania University, Hyderabad-500007, India

Cite this paper

R. Sanjeev, D. A. Padmavati and V. Jagannadham. Why the Second Bond Exceptionally Effective on pK_a Values of -ynoic (-C≡C-) Compounds? Chemical Education Perspective. World Journal of Chemical Education. 2021; 9(3):94-95. doi: 10.12691/WJCE-9-3-5

Abstract

Sudden decrease of nearly more than two orders of magnitude of pK_a units of ynoic series of compounds is explained based on the electronegativity differences of sp, sp2 and sp3 carbons and on the subsequent stability of the corresponding anions. Both resonance and inductive effects operate in tandem to stabilize the ynoic anions.

Keywords

Ynoic compounds, chemical education, graduate research; pH and pK_a

Copyright

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References

[1]	Sørensen, S. P. L. (1909). Biochem. Z. 21: 131-304.
[2]	pKa values are from Lange’s Handbook of Chemistry, Ed. by John A. Dean, 15th Edition, McGraw-Hill, Inc. New York, 1999.
[3]	Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 5-88.
[4]	J. March, Advanced Organic Chemistry, Reactions, Mechanisms, and Structure, 4th Edition, Wiley Interscience, 1992, page 269.