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♦
38.7k7113235
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
926
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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♦
38.7k7113235
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
926
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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♦
38.7k7113235
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
926
$endgroup$
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♦
38.7k7113235
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
926
edited Dec 23 '18 at 22:51
orthocresol♦
38.7k7113235
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
926
edited Dec 23 '18 at 22:51
orthocresol♦
38.7k7113235
edited Dec 23 '18 at 22:51
orthocresol♦
38.7k7113235
edited Dec 23 '18 at 22:51
orthocresol♦
38.7k7113235
38.7k7113235
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
926
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
926
asked Dec 16 '18 at 10:20
Saheb Garain great chemistSaheb Garain great chemist
926
926
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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
380213
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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♦
38.7k7113235
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
92119
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2 Answers
2
active
oldest
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2 Answers
2
active
oldest
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active
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active
oldest
votes
$begingroup$
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
380213
$endgroup$
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
380213
$endgroup$
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
380213
$endgroup$
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
380213
edited Dec 16 '18 at 16:57
answered Dec 16 '18 at 16:09
YUSUF HASANYUSUF HASAN
380213
answered Dec 16 '18 at 16:09
YUSUF HASANYUSUF HASAN
380213
answered Dec 16 '18 at 16:09
YUSUF HASANYUSUF HASAN
380213
380213
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♦
38.7k7113235
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
92119
$endgroup$
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♦
38.7k7113235
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
92119
$endgroup$
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♦
38.7k7113235
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
92119
$endgroup$
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♦
38.7k7113235
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
92119
edited Dec 24 '18 at 0:34
orthocresol♦
38.7k7113235
edited Dec 24 '18 at 0:34
orthocresol♦
38.7k7113235
edited Dec 24 '18 at 0:34
orthocresol♦
38.7k7113235
38.7k7113235
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
92119
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
92119
answered Dec 16 '18 at 13:46
Organic Chemistry ExplainedOrganic Chemistry Explained
92119
92119
add a comment |
add a comment |
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– orthocresol♦
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