330:
478:
160:
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220:
showed that it was in the zwitterionic form in the solid state and confirmed the presence of hydrogen bonds. Theoretical calculations have been used to show that zwitterions may also be present in the gas phase for some cases different from the simple carboxylic acid-to-amine transfer.
404:
Because tautomers are different compounds, they sometimes have different enough structures that they can be detected independently in their mixture. This allows experimental analysis of the equilibrium.
444:
Other examples of permanent zwitterions include phosphatidylcholines, which also contain a quaternary nitrogen atom, but with a negatively-charged phosphate group in place of a carboxylate group;
437:
link. At the present time, all compounds whose structure includes this motif are known as betaines. Betaines do not isomerize because the chemical groups attached to the nitrogen atom are not
477:
845:
Cotrait, Par Michel (1972). "La structure cristalline de l'acide éthylènediamine tétraacétique, EDTA" [The crystalline structure of ethylenediamine tetraacetic acid, EDTA].
907:
Nagy, Peter I.; Takács-Novák, Krisztina (1997). "Theoretical and
Experimental Studies of the Zwitterion ⇌ Neutral Form Equilibrium of Ampholytes in Pure Solvents and Mixtures".
568:
872:
Kiruba, G. S. M.; Ming, Wah Wong (2003). "Tautomeric
Equilibria of Pyridoxal-5′-phosphate and 3-Hydroxypyridine Derivatives: A Theoretical Study of Solvation Effects".
401:, in aqueous solution is predicted to have an equilibrium favoring a tautomeric form in which a proton is transferred from the phenolic -OH group to the nitrogen atom.
678:"Precision neutron diffraction structure determination of protein and nucleic acid components. III. The crystal and molecular structure of the amino acid α-glycine"
514:
character, activate strong bonds and small molecules, and serve as transient intermediates in catalysis. Donor-acceptor entities are of vast use in photochemistry (
329:
281:
655:
243:. This is also consistent with the zwitterion being the predominant isomer that is present in an aqueous solution. For comparison, the simple carboxylic acid
441:. These compounds may be classed as permanent zwitterions, as isomerisation to a molecule with no electrical charges does not occur, or is very slow.
394:
Insight to the equilibrium in solution may be gained from the results of theoretical calculations. For example, pyridoxal phosphate, a form of
616:
700:
943:
598:
74:
462:
560:
515:
453:
167:
contains both acidic (carboxylic acid fragment) and basic (amine fragment) centres. The isomer on the right is a zwitterion.
208:
It has been suggested, on the basis of theoretical analysis, that the zwitterion is stabilized in aqueous solution by
492:
159:
635:
310:
225:
95:
367:
is a zwitterion with two protons having been transferred from carboxylic acid groups to the nitrogen atoms.
296:
1006:
Munz, Dominik; Karsten, Meyer (2021). "Charge frustration in ligand design and functional group transfer".
421:, was named as "betaine". Later, other compounds were discovered that contain the same structural motif, a
498:
422:
126:
1047:
449:
510:
Strongly polarized conjugated compounds (conjugated zwitterions) are typically very reactive, share
519:
484:
213:
140:
1023:
677:
523:
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349:
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118:
30:
430:
83:
448:, which contain a quaternary nitrogen atom and a negatively charged sulfonate group; and
750:
725:
244:
961:"Solubilization of membrane proteins by sulfobetaines, novel zwitterionic surfactants"
960:
1041:
1027:
976:
342:
287:
136:
102:
386:
378:
and may jump to the phosphate group to form a compound which is not a zwitterion.
589:
Skoog, Douglas A.; West, Donald M.; Holler, F. James; Crouch, Stanley R. (2004).
201:
The ratio of the concentrations of the two species in solution is independent of
89:
636:"On the Number of Water Molecules Necessary to Stabilize the Glycine Zwitterion"
535:
426:
148:
144:
1019:
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831:
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16:
Molecule containing an equal number of positive and negative functional groups
984:
511:
456:. Lauramidopropyl betaine is the major component of cocamidopropyl betaine.
353:
20:
893:
759:
992:
375:
139:
to an all-neutral form, such as when the positive charge is located on a
114:
651:
775:"A neutron diffraction study on the crystal structure of sulfamic acid"
235:
for deprotonation of the common amino acids span the approximate range
217:
132:
920:
885:
741:
129:
will be established between the "parent" molecule and the zwitterion.
438:
724:
Price, William D.; Jockusch, Rebecca A.; Williams, Evan R. (1997).
117:
that contains an equal number of positively and negatively charged
593:(8th ed.). Thomson/Brooks/Cole. pp. 231, 385, 419, 460.
360:
317:
356:. One molecule is in the zwitterion form, the other is not.
202:
63:
60:
51:
45:
806:
Brown, C. J.; Ehrenberg, M. (1985). "Anthranilic acid, C
171:
Tautomerism of amino acids follows this stoichiometry:
75:
66:
54:
39:
57:
48:
42:
36:
33:
8:
959:Gonenne, Amnon; Ernst, Robert (1978-06-15).
938:(3rd ed.). New York: Worth Publishing.
726:"Is Arginine a Zwitterion in the Gas Phase?"
374:, the proton on the dimethyl amino group is
212:with solvent water molecules. Analysis of
143:group. Similarly, a molecule containing a
790:
749:
730:Journal of the American Chemical Society
640:Journal of the American Chemical Society
634:Jensen, Jan H.; Gordon, Mark S. (1995).
611:(9th ed.). 2013. pp. 415–416.
385:
258:
254:
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185:
181:
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458:
277:
936:Lehninger, Principles of Biochemistry
345:crystallizes in the zwitterion form.
94:
7:
609:Fundamentals of Analytical Chemistry
591:Fundamentals of Analytical Chemistry
290:isomers, with the zwitterion (right)
934:Nelson, D. L.; Cox, M. M. (2000).
676:Jönsson, P.-G.; Kvick, Å. (1972).
14:
685:Acta Crystallographica Section B
491:
476:
461:
328:
309:
295:
280:
29:
706:from the original on 2020-03-14
658:from the original on 2020-12-02
571:from the original on 2023-06-21
352:there are two molecules in the
516:photoinduced electron transfer
454:dipalmitoylphosphatidylcholine
409:Betaines and similar compounds
1:
125:, for example, in solution a
977:10.1016/0003-2697(78)90565-1
874:Journal of Organic Chemistry
135:are zwitterions that cannot
818:, by neutron diffraction".
429:group attached to it via a
1064:
1020:10.1038/s41570-021-00276-3
417:, which was isolated from
859:10.1107/S056774087200319X
832:10.1107/S0108270185004206
792:10.1107/S0365110X60000789
697:10.1107/S0567740872005096
847:Acta Crystallographica B
820:Acta Crystallographica C
151:group cannot isomerize.
965:Analytical Biochemistry
779:Acta Crystallographica
506:Conjugated zwitterions
499:cocamidopropyl betaine
471:(trivial name betaine)
391:
168:
88:
450:pulmonary surfactants
425:nitrogen atom with a
389:
162:
773:Sass, R. L. (1960).
565:Chemistry LibreTexts
359:In the solid state,
127:chemical equilibrium
736:(49): 11988–11989.
652:10.1021/ja00136a013
520:organic electronics
485:phosphatidylcholine
390:pyridoxal phosphate
382:Theoretical studies
214:neutron diffraction
141:quaternary ammonium
105:'), also called an
392:
169:
921:10.1021/ja963512f
915:(21): 4999–5006.
886:10.1021/jo0266792
742:10.1021/ja9711627
646:(31): 8159–8170.
618:978-1-285-60719-1
119:functional groups
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561:"Zwitterion"
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184:H ⇌ RCH(NH
170:
147:group and a
131:
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99:
87:
24:
18:
1048:Zwitterions
536:Amphoterism
427:carboxylate
155:Amino acids
149:carboxylate
145:phosphonium
123:amino acids
111:dipolar ion
82:; from
710:2019-09-03
662:2020-08-28
575:2022-02-11
547:References
423:quaternary
419:sugar beet
372:psilocybin
336:Psilocybin
165:amino acid
107:inner salt
25:zwitterion
1028:235220781
985:0003-2697
512:diradical
396:vitamin B
354:unit cell
263:) has a p
216:data for
137:isomerize
21:chemistry
1042:Category
894:12662064
760:16479267
701:Archived
656:Archived
569:Archived
530:See also
452:such as
133:Betaines
115:molecule
79:-ə-ry-ən
751:1364450
524:sensing
218:glycine
121:. With
113:, is a
101: '
90:Zwitter
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993:677454
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983:
942:
892:
758:
748:
615:
597:
439:labile
376:labile
233:values
176:RCH(NH
84:German
1024:S2CID
704:(PDF)
681:(PDF)
86:
77:TSVIT
989:PMID
981:ISSN
940:ISBN
890:PMID
756:PMID
613:ISBN
595:ISBN
365:EDTA
322:EDTA
237:2.15
224:The
23:, a
1016:doi
973:doi
917:doi
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855:doi
828:doi
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370:In
241:0.2
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180:)CO
163:An
109:or
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253:CH
249:CH
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203:pH
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