Do non-classical carbanions exist?
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There are some non-classical carbocations, such as the 2-norbornyl cation, in which the positive charge is heavily delocalised. Have non-classical carbanions also been discovered? I have not seen any non-classical carbanions in books. If there are any non-classical carbanions, please provide some examples.
organic-chemistry ions resonance
edited Dec 23 '18 at 22:51
orthocresol♦
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asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
916
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There are some non-classical carbocations, such as the 2-norbornyl cation, in which the positive charge is heavily delocalised. Have non-classical carbanions also been discovered? I have not seen any non-classical carbanions in books. If there are any non-classical carbanions, please provide some examples.
organic-chemistry ions resonance
edited Dec 23 '18 at 22:51
orthocresol♦
38.9k7113237
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
916
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– orthocresol♦
Dec 24 '18 at 2:26
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There are some non-classical carbocations, such as the 2-norbornyl cation, in which the positive charge is heavily delocalised. Have non-classical carbanions also been discovered? I have not seen any non-classical carbanions in books. If there are any non-classical carbanions, please provide some examples.
organic-chemistry ions resonance
edited Dec 23 '18 at 22:51
orthocresol♦
38.9k7113237
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
916
$endgroup$
There are some non-classical carbocations, such as the 2-norbornyl cation, in which the positive charge is heavily delocalised. Have non-classical carbanions also been discovered? I have not seen any non-classical carbanions in books. If there are any non-classical carbanions, please provide some examples.
organic-chemistry ions resonance
organic-chemistry ions resonance
edited Dec 23 '18 at 22:51
orthocresol♦
38.9k7113237
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
916
edited Dec 23 '18 at 22:51
orthocresol♦
38.9k7113237
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
916
edited Dec 23 '18 at 22:51
orthocresol♦
38.9k7113237
edited Dec 23 '18 at 22:51
orthocresol♦
38.9k7113237
edited Dec 23 '18 at 22:51
orthocresol♦
38.9k7113237
38.9k7113237
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
916
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
916
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
916
916
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If an answer has helped solve your question, please consider upvoting and/or accepting one (by clicking on the tick next to the voting buttons). That's the Stack Exchange way of saying thank you! See also: chemistry.stackexchange.com/help/someone-answers
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– orthocresol♦
Dec 24 '18 at 2:26
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– orthocresol♦
Dec 24 '18 at 2:26
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– orthocresol♦
Dec 24 '18 at 2:26
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2 Answers
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In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered Dec 16 '18 at 16:09
YUSUF HASANYUSUF HASAN
4051214
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1
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Please give me some references
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– Saheb Garain great chemist
Dec 16 '18 at 16:32
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Interesting question. It is much less studied and reported on than the case of non-classical carbocations, but I did find a few papers. Brown and Occolowitz (Brown, J. M.; Occolowitz, J. L. Chem. Commun. 1965, 376–377) reported that deuterated bicyclo[3.2.1]octa-2,6-diene 1b, below, undergoes base-catalysed de-deuteration (potassium tert-butoxide in DMSO) to give 1a much faster (ca. 3 x 10^4) than the bicyclo[3.2.1]octa-2-ene counterpart, ie. 2b -> 2a. They suggested this is evidence for the intermediacy of a 6π-electron, delocalised (non-classical) carbanion 3.
Much more recently, Brown reviewed and provided additional DFT computational evidence for stabilisation and charge delocalisation in these species (Brown, J. M. Aust. J. Chem. 2014, 67, 1296–1300).
edited Dec 24 '18 at 0:34
orthocresol♦
38.9k7113237
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
95119
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2 Answers
2
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oldest
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2 Answers
2
active
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active
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$begingroup$
In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered Dec 16 '18 at 16:09
YUSUF HASANYUSUF HASAN
4051214
$endgroup$
1
$begingroup$
Please give me some references
$endgroup$
– Saheb Garain great chemist
Dec 16 '18 at 16:32
add a comment |
$begingroup$
In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered Dec 16 '18 at 16:09
YUSUF HASANYUSUF HASAN
4051214
$endgroup$
1
$begingroup$
Please give me some references
$endgroup$
– Saheb Garain great chemist
Dec 16 '18 at 16:32
add a comment |
$begingroup$
In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered Dec 16 '18 at 16:09
YUSUF HASANYUSUF HASAN
4051214
$endgroup$
In addition to the species mentioned in the answer above, I found another one in Organic Chemistry by Morrison and Boyd(Seventh Edition)
answered Dec 16 '18 at 16:09
YUSUF HASANYUSUF HASAN
4051214
edited Dec 16 '18 at 16:57
answered Dec 16 '18 at 16:09
YUSUF HASANYUSUF HASAN
4051214
answered Dec 16 '18 at 16:09
YUSUF HASANYUSUF HASAN
4051214
answered Dec 16 '18 at 16:09
YUSUF HASANYUSUF HASAN
4051214
4051214
1
$begingroup$
Please give me some references
$endgroup$
– Saheb Garain great chemist
Dec 16 '18 at 16:32
add a comment |
1
$begingroup$
Please give me some references
$endgroup$
– Saheb Garain great chemist
Dec 16 '18 at 16:32
1
1
$begingroup$
Please give me some references
$endgroup$
– Saheb Garain great chemist
Dec 16 '18 at 16:32
$begingroup$
Please give me some references
$endgroup$
– Saheb Garain great chemist
Dec 16 '18 at 16:32
add a comment |
$begingroup$
Interesting question. It is much less studied and reported on than the case of non-classical carbocations, but I did find a few papers. Brown and Occolowitz (Brown, J. M.; Occolowitz, J. L. Chem. Commun. 1965, 376–377) reported that deuterated bicyclo[3.2.1]octa-2,6-diene 1b, below, undergoes base-catalysed de-deuteration (potassium tert-butoxide in DMSO) to give 1a much faster (ca. 3 x 10^4) than the bicyclo[3.2.1]octa-2-ene counterpart, ie. 2b -> 2a. They suggested this is evidence for the intermediacy of a 6π-electron, delocalised (non-classical) carbanion 3.
Much more recently, Brown reviewed and provided additional DFT computational evidence for stabilisation and charge delocalisation in these species (Brown, J. M. Aust. J. Chem. 2014, 67, 1296–1300).
edited Dec 24 '18 at 0:34
orthocresol♦
38.9k7113237
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
95119
$endgroup$
add a comment |
$begingroup$
Interesting question. It is much less studied and reported on than the case of non-classical carbocations, but I did find a few papers. Brown and Occolowitz (Brown, J. M.; Occolowitz, J. L. Chem. Commun. 1965, 376–377) reported that deuterated bicyclo[3.2.1]octa-2,6-diene 1b, below, undergoes base-catalysed de-deuteration (potassium tert-butoxide in DMSO) to give 1a much faster (ca. 3 x 10^4) than the bicyclo[3.2.1]octa-2-ene counterpart, ie. 2b -> 2a. They suggested this is evidence for the intermediacy of a 6π-electron, delocalised (non-classical) carbanion 3.
Much more recently, Brown reviewed and provided additional DFT computational evidence for stabilisation and charge delocalisation in these species (Brown, J. M. Aust. J. Chem. 2014, 67, 1296–1300).
edited Dec 24 '18 at 0:34
orthocresol♦
38.9k7113237
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
95119
$endgroup$
add a comment |
$begingroup$
Interesting question. It is much less studied and reported on than the case of non-classical carbocations, but I did find a few papers. Brown and Occolowitz (Brown, J. M.; Occolowitz, J. L. Chem. Commun. 1965, 376–377) reported that deuterated bicyclo[3.2.1]octa-2,6-diene 1b, below, undergoes base-catalysed de-deuteration (potassium tert-butoxide in DMSO) to give 1a much faster (ca. 3 x 10^4) than the bicyclo[3.2.1]octa-2-ene counterpart, ie. 2b -> 2a. They suggested this is evidence for the intermediacy of a 6π-electron, delocalised (non-classical) carbanion 3.
Much more recently, Brown reviewed and provided additional DFT computational evidence for stabilisation and charge delocalisation in these species (Brown, J. M. Aust. J. Chem. 2014, 67, 1296–1300).
edited Dec 24 '18 at 0:34
orthocresol♦
38.9k7113237
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
95119
$endgroup$
Interesting question. It is much less studied and reported on than the case of non-classical carbocations, but I did find a few papers. Brown and Occolowitz (Brown, J. M.; Occolowitz, J. L. Chem. Commun. 1965, 376–377) reported that deuterated bicyclo[3.2.1]octa-2,6-diene 1b, below, undergoes base-catalysed de-deuteration (potassium tert-butoxide in DMSO) to give 1a much faster (ca. 3 x 10^4) than the bicyclo[3.2.1]octa-2-ene counterpart, ie. 2b -> 2a. They suggested this is evidence for the intermediacy of a 6π-electron, delocalised (non-classical) carbanion 3.
Much more recently, Brown reviewed and provided additional DFT computational evidence for stabilisation and charge delocalisation in these species (Brown, J. M. Aust. J. Chem. 2014, 67, 1296–1300).
edited Dec 24 '18 at 0:34
orthocresol♦
38.9k7113237
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
95119
edited Dec 24 '18 at 0:34
orthocresol♦
38.9k7113237
edited Dec 24 '18 at 0:34
orthocresol♦
38.9k7113237
edited Dec 24 '18 at 0:34
orthocresol♦
38.9k7113237
38.9k7113237
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
95119
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
95119
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
95119
95119
add a comment |
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– orthocresol♦
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