Is phosphorine (C₅H₅P) aromatic?
11
$begingroup$
Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?
aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds
edited Nov 24 '18 at 19:50
Mithoron
3,60582845
asked Nov 23 '18 at 15:34
user137644user137644
1035
$endgroup$
add a comment |
11
$begingroup$
Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?
aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds
edited Nov 24 '18 at 19:50
Mithoron
3,60582845
asked Nov 23 '18 at 15:34
user137644user137644
1035
$endgroup$
3
$begingroup$
Phosphinine is aromatic, but somewhat less than benzene.
$endgroup$
– mykhal
Nov 23 '18 at 16:23
add a comment |
11
11
11
$begingroup$
Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?
aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds
edited Nov 24 '18 at 19:50
Mithoron
3,60582845
asked Nov 23 '18 at 15:34
user137644user137644
1035
$endgroup$
Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?
aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds
aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds
edited Nov 24 '18 at 19:50
Mithoron
3,60582845
asked Nov 23 '18 at 15:34
user137644user137644
1035
edited Nov 24 '18 at 19:50
Mithoron
3,60582845
asked Nov 23 '18 at 15:34
user137644user137644
1035
edited Nov 24 '18 at 19:50
Mithoron
3,60582845
edited Nov 24 '18 at 19:50
Mithoron
3,60582845
edited Nov 24 '18 at 19:50
Mithoron
3,60582845
3,60582845
asked Nov 23 '18 at 15:34
user137644user137644
1035
asked Nov 23 '18 at 15:34
user137644user137644
1035
asked Nov 23 '18 at 15:34
user137644user137644
1035
1035
3
$begingroup$
Phosphinine is aromatic, but somewhat less than benzene.
$endgroup$
– mykhal
Nov 23 '18 at 16:23
add a comment |
3
$begingroup$
Phosphinine is aromatic, but somewhat less than benzene.
$endgroup$
– mykhal
Nov 23 '18 at 16:23
3
3
$begingroup$
Phosphinine is aromatic, but somewhat less than benzene.
$endgroup$
– mykhal
Nov 23 '18 at 16:23
$begingroup$
Phosphinine is aromatic, but somewhat less than benzene.
$endgroup$
– mykhal
Nov 23 '18 at 16:23
add a comment |
1 Answer
1
active
oldest
votes
13
$begingroup$
Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.
edited Nov 24 '18 at 21:15
Waylander
6,26111323
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
15.4k12647
$endgroup$
1
$begingroup$
With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38
$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38
1
$begingroup$
No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22
add a comment |
Your Answer
StackExchange.ifUsing("editor", function () {
return StackExchange.using("mathjaxEditing", function () {
StackExchange.MarkdownEditor.creationCallbacks.add(function (editor, postfix) {
StackExchange.mathjaxEditing.prepareWmdForMathJax(editor, postfix, [["$", "$"], ["\\(","\\)"]]);
});
});
}, "mathjax-editing");
StackExchange.ready(function() {
var channelOptions = {
tags: "".split(" "),
id: "431"
};
initTagRenderer("".split(" "), "".split(" "), channelOptions);
StackExchange.using("externalEditor", function() {
// Have to fire editor after snippets, if snippets enabled
if (StackExchange.settings.snippets.snippetsEnabled) {
StackExchange.using("snippets", function() {
createEditor();
});
}
else {
createEditor();
}
});
function createEditor() {
StackExchange.prepareEditor({
heartbeatType: 'answer',
autoActivateHeartbeat: false,
convertImagesToLinks: false,
noModals: true,
showLowRepImageUploadWarning: true,
reputationToPostImages: null,
bindNavPrevention: true,
postfix: "",
imageUploader: {
brandingHtml: "Powered by u003ca class="icon-imgur-white" href="https://imgur.com/"u003eu003c/au003e",
contentPolicyHtml: "User contributions licensed under u003ca href="https://creativecommons.org/licenses/by-sa/3.0/"u003ecc by-sa 3.0 with attribution requiredu003c/au003e u003ca href="https://stackoverflow.com/legal/content-policy"u003e(content policy)u003c/au003e",
allowUrls: true
},
onDemand: true,
discardSelector: ".discard-answer"
,immediatelyShowMarkdownHelp:true
});
}
});
draft saved
draft discarded
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
StackExchange.ready(
function () {
StackExchange.openid.initPostLogin('.new-post-login', 'https%3a%2f%2fchemistry.stackexchange.com%2fquestions%2f104725%2fis-phosphorine-c%25e2%2582%2585h%25e2%2582%2585p-aromatic%23new-answer', 'question_page');
}
);
Post as a guest
Required, but never shown
1 Answer
1
active
oldest
votes
1 Answer
1
active
oldest
votes
active
oldest
votes
active
oldest
votes
13
$begingroup$
Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.
edited Nov 24 '18 at 21:15
Waylander
6,26111323
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
15.4k12647
$endgroup$
1
$begingroup$
With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38
$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38
1
$begingroup$
No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22
add a comment |
13
$begingroup$
Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.
edited Nov 24 '18 at 21:15
Waylander
6,26111323
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
15.4k12647
$endgroup$
1
$begingroup$
With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38
$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38
1
$begingroup$
No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22
add a comment |
13
13
13
$begingroup$
Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.
edited Nov 24 '18 at 21:15
Waylander
6,26111323
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
15.4k12647
$endgroup$
Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.
edited Nov 24 '18 at 21:15
Waylander
6,26111323
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
15.4k12647
edited Nov 24 '18 at 21:15
Waylander
6,26111323
edited Nov 24 '18 at 21:15
Waylander
6,26111323
edited Nov 24 '18 at 21:15
Waylander
6,26111323
6,26111323
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
15.4k12647
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
15.4k12647
answered Nov 23 '18 at 16:26
Oscar LanziOscar Lanzi
15.4k12647
15.4k12647
1
$begingroup$
With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38
$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38
1
$begingroup$
No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22
add a comment |
1
$begingroup$
With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38
$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38
1
$begingroup$
No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22
1
1
$begingroup$
With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38
$begingroup$
With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38
$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38
$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38
1
1
$begingroup$
No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22
$begingroup$
No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22
add a comment |
draft saved
draft discarded
Thanks for contributing an answer to Chemistry Stack Exchange!
- Please be sure to answer the question. Provide details and share your research!
But avoid …
- Asking for help, clarification, or responding to other answers.
- Making statements based on opinion; back them up with references or personal experience.
Use MathJax to format equations. MathJax reference.
To learn more, see our tips on writing great answers.
draft saved
draft discarded
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
StackExchange.ready(
function () {
StackExchange.openid.initPostLogin('.new-post-login', 'https%3a%2f%2fchemistry.stackexchange.com%2fquestions%2f104725%2fis-phosphorine-c%25e2%2582%2585h%25e2%2582%2585p-aromatic%23new-answer', 'question_page');
}
);
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
3
$begingroup$
Phosphinine is aromatic, but somewhat less than benzene.
$endgroup$
– mykhal
Nov 23 '18 at 16:23