Specific energy contributions from competing hydrogen-bonded structures in six polymorphs of phenobarbital

Gelbrich, Thomas; Braun, Doris E.; Griesser, Ulrich J.

doi:10.1186/s13065-016-0152-5

BMC Chemistry

Table 1 N–H···O=C bonded chain (C-1 to C-5), layer (L-1 to L-6) and framework (F-1, F-2) structures found in solid forms of barbituric acid and its 5-substituted derivatives

From: Specific energy contributions from competing hydrogen-bonded structures in six polymorphs of phenobarbital

R⁵	R^5′	Common name(s)	Form	Motif	CSD refcode	References
Methyl	Methyl			C-1	NUXTAC	[63]
Ethyl	Isopropyl	Ipral	I	C-1	FUFTAC	[25]
Ethyl	Butyl	Soneryl, butobarbital	RT-Form	C-1	ETBBAR	[64]
Ethyl	Butyl	Soneryl, butobarbital	LT-Form	C-1	ETBBAR01	[65]
Ethyl	Butyl	Soneryl, butobarbital		C-1	ETBBAR02	[66]
Allyl	Isobutyl	Sandoptal		C-1	FUFTIK	[25]
Ethyl	Pentan-2-yl	Pentobarbital, nembutal	I	C-1	FUFTEG01	[48]
Ethyl	Pentan-2-yl	Pentobarbital, nembutal	II	C-1	FUFTEG04	[48]
Ethyl	Pentan-2-yl or phenyl	^a	co-crystal	C-1	LATMEA	[48]
Ethyl	n-pentyl			C-1	ENPBAR	[67]
Ethyl	Isopentyl	Amobarbital	II^b	C-1	AMYTAL10	[68]
Ethyl	Isopentyl	Amobarbital	I^b	C-1	AMYTAL11	[68]
Ethyl	But-2-enyl			C-1	BEBWUA	[69]
Ethyl	3-Methylbut-2-enyl			C-1	BECLIE	[70]
Ethyl	1,3-Dimethylbut-1-enyl			C-1	BEBWOU	[71]
Ethyl	1,3-Dimethylbut-2-enyl			C-1	JIFRIZ	[72]
Ethyl	1,3-Dimethylbutyl	α-Methylamobarbital		C-1	MAOBAR	[73]
Ethyl	Phenyl	Phenobarbital	CH₃CN solvate	C-1	–	[35]
Ethyl	Phenyl	Phenobarbital	CH₃NO₂ solvate	C-1	–	[35]
Ethyl	1-Cyclohexen-1-yl	Phanodorm		C-1	ETCYBA01	[25]
Ethyl	Cyclohexyl		II	C-1	YOZJUU01	[49]
Allyl	Allyl	Dial		C-1	DALLBA	[74]
Allyl	Isopropyl	Aprobarbital	I	C-1	AIPBAR	[75]
F	Phenyl			C-2	HEKTOG	[47]
Ethyl	Ethyl	Barbital	II	C-2	DETBAA02	[76]
Ethyl	Pentan-2-yl	Pentobarbital, nembutal	III	C-2	FUFTEG02	[48]
Ethyl	Phenyl	Phenobarbital	III	C-2	PHBARB09	[26]
Ethyl	Phenyl	Phenobarbital	CH₂Cl₂ solvate	C-2	–	[35]
Ethyl	6-Oxocyclohexenyl	6-Oxocyclobarbital		C-2	OXCBAR	[77]
Cl	Cl		III	C-3	UXIYOQ02	[78]
Ethyl	3,3-Dimethyl-n-butyl	γ-Methylamobarbital		C-3	EMBBAR20	[79]
Ethyl	Phenyl	Phenobarbital	V	C-3	–	This work
Allyl	Phenyl	Alphenal		C-3	FUFSOP	[25]
Propenyl	1-Methylbutyl	Quinal barbitone		C-3	TICFER	[80]
H	H	Barbituric acid	I	C-4	BARBAC01	[46]
H	Ethyl		I	C-4	ETBARB	[81]
Methyl	Phenyl	Rutonal, heptobarbital	I	C-4	MPBRBL01	[25]
Methyl	Phenyl	Rutonal, heptobarbital	II	C-4	MPBRBL	[82]
Ethyl	Ethyl	Barbital	I	C-4	DETBAA01	[76]
Allyl	Cyclopent-2-en-1-yl	Cyclopal	I	C-4	FUFSUV	[25]
Ethyl	Butyl	Soneryl, butobarbital		C-4 + C-3	ETBBAR03	[83]
Ethyl	Phenyl	Phenobarbital	VI	C-5	–	This work
Ethyl	Ethyl	Barbital	IV	L-1	DETBAA03	[84]
Ethyl	Pentan-2-yl	Pentobarbital, nembutal	IV	L-1	FUFTEG03	[48]
Ethyl	1-Methylbutenyl	Vinbarbital		L-1	VINBAR	[85]
Ethyl	1-Cyclohepten-1-yl	Medomin		L-1	CHEBAR01	[25]
H	H	Barbituric acid	II	L-2	BARBAC02	[46]
Ethyl	Phenyl	Phenobarbital	I	L-3 + C-2	PHBARB07	[26]
Ethyl	Phenyl	Phenobarbital	II	L-3 + C-2	PHBARB08	[26]
Ethyl	Cyclohexyl		I	L-4	YOZJUU	[49]
Isopropyl	2-Bromoallyl	Noctal	II	L-4	UXIYIK	[23]
Cl	Cl		I	L-5	UXIYOQ	[23]
Cl	Cl		II	L-6	UXIYOQ01	[23]
Br	Br		I	L-6	UXIZAD	[23]
F	F			F-1	HEKTIA	[47]
Br	Br		II	F-2	UXIZAD01	[23]

See Fig. 2 and Ref. [23] for graphical representations. R⁵ and R^5′ are the substituents at ring position 5
^aCo-crystal of phenobarbital and pentobarbital
^bNomenclature according to Ref. [25]

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ISSN: 2661-801X

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