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Jun 18, 2019 at 22:55 comment added Martin - マーチン Atoms cannot be hybridised, only orbitals can. Therefore it is incorrect to state N is sp² hybridised, even though it is used in that way (too) often. Consider it lab jargon.
Jun 18, 2019 at 22:55 comment added Andrew In the paper you linked, the bond lengths are given as 1.351, 1.340 and 1.322. That’s identical as far as I’m concerned. Compare to the C-N bond of the primary amine at 1.48. Clearly a difference in bond order.
Jun 18, 2019 at 22:34 comment added Cyclopropane @Andrew, what do you mean "All C-N bonds are identical within error"?
Jun 18, 2019 at 22:26 history edited Mathew Mahindaratne CC BY-SA 4.0
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Jun 18, 2019 at 22:16 vote accept Cyclopropane
Jun 18, 2019 at 21:51 answer added Mathew Mahindaratne timeline score: 3
Jun 18, 2019 at 21:01 comment added Andrew The paper you linked with the reference to quantum mechanical calculations appears to be instead a description of a crystal structure doped with arginine. In that structure the C-N bonds are identical within error, and the guanidino group is described as planar, so all sp2 hybridized.
Jun 18, 2019 at 20:35 history edited Mithoron CC BY-SA 4.0
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Jun 18, 2019 at 20:04 comment added electronpusher Have you considered resonance?
Jun 18, 2019 at 19:43 history asked Cyclopropane CC BY-SA 4.0