Coordination propensity of N-protected amino acids and sterically congested heterocyclic  β-diketones toward BuSnCl3: preparation and structural features of some new seven coordinated organic-inorganic hybrid formulations of monobutyltin(IV)

Manish Kumar Srivastava; Asha Jain; Sanjiv Saxena

doi:10.1515/mgmc-2014-0001

Article Open Access

Coordination propensity of N-protected amino acids and sterically congested heterocyclic β-diketones toward BuSnCl₃: preparation and structural features of some new seven coordinated organic-inorganic hybrid formulations of monobutyltin(IV)

Manish Kumar Srivastava , Asha Jain and Sanjiv Saxena

Published/Copyright: July 19, 2014

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From the journal Main Group Metal Chemistry Volume 37 Issue 3-4

Abstract

A new set of N-protected amino acids and sterically congested heterocyclic β-diketones-modified BuSnCl₃ formulations having the general formulae BuSnClAL, where [where -CHR=-CH₂ CH₂,R= -CH(CH₃)CH₂ CH₃] and [where R′=-C₆ H₅, -CH₃, -pClC₆ H₄] and BuSn(A)₂ L, where [where -CHR=-CH₂ CH₂, R=- CH(CH₃)CH₂ CH₃] and [where R′=-C₆ H₅, -CH₃, -pClC₆ H₄] were prepared by the reactions of monobutyltin(IV) chloride with sodium salts of N-protected amino acids and sterically congested heterocyclic β-diketones in 1:1:1 and 1:2:1 molar ratios in refluxing dry THF. Plausible structures of these N-protected amino acids and sterically congested heterocyclic β-diketones-modified BuSnCl₃ formulations were suggested on the basis of physicochemical and spectral studies. These newly prepared organic-inorganic hybrid complexes of monobutyltin(IV) contain seven coordinated tin centers as revealed by ¹¹⁹Sn NMR spectral data.

Keywords: BuSnCl3; heterocyclic β-diketones; N-protected amino acids; spectral studies

Introduction

The synthetic and structural chemistry of organic-inorganic hybrid complexes of organotin(IV) has generated extensive interest due to their technological (Davies, 2010), industrial (Ahmad et al., 2000), and agricultural applications (Aziz-ur-Rehman et al., 2011). Organotin(IV) complexes find applications as wood preservatives (Kizlink et al., 1996), marine antifouling paints (Singh et al., 2011), fungicides (Kizlink, 1991; Dylag et al., 2010; Khan et al., 2010; Mishra et al., 2011), bactericides (Abbas et al., 2013; Sedaghat et al., 2013a,b), surface disinfectants (Singh et al., 2011), and are used as drugs like NASAIDs (Dokorou et al., 2008), etc. It is well documented that organic-inorganic hybrid complexes of organotin(IV) possess superior properties (Najafi et al., 2013), which are important for the technological application of these materials. In order to study the coordination propensity of N-protected amino acids and sterically congested heterocyclic β-diketones toward BuSnCl₃, the reactions of these ligands were carried out with BuSnCl₃. The interaction of BuSnCl₃ with N-protected amino acids and sterically congested heterocyclic β-diketones afforded some new organic-inorganic hybrid formulations of BuSnCl₃. It is pertinent and interesting to study the effect of the potentially bridging chlorine atom (Davies et al., 1970; Lefferts et al., 1982) on the structure and properties of these materials.

Results and discussion

A number of N-protected amino acids and sterically congested heterocyclic β-diketone-modified BuSnCl₃ formulations having the general formulae BuSnClAL, where [where -CHR=-CH₂ CH₂,R=-CH(CH₃)CH₂ CH₃] and LH= [where R′=-C₆ H₅, -CH₃, -pClC₆ H₄] and BuSn[(A)₂ L], where [where -CHR=-CH₂ CH₂,R=-CH(CH₃)CH₂ CH₃] and [where R′=-C₆ H₅, -CH₃, -pClC₆ H₄] were synthesized by the interaction of BuSnCl₃ with sodium salts of N-protected amino acids and sterically congested heterocyclic β-diketones in 1:1:1 (Scheme 1) and 1:2:1 (Scheme 2) molar ratios in refluxing dry THF solution.

Scheme 1

where

-CHR=-CH₂ CH₂, R′=-C₆ H₅, BuSnCl[A₁ L₁], Complex 1

-CHR=-CH₂ CH₂, R′=-CH₃, BuSnCl[A₁ L₃], Complex 2

R=-CH(CH₃)CH₂ CH₃, R′=-C₆ H₅, BuSnCl[A₂ L₁], Complex 3

R=-CH(CH₃)CH₂ CH₃, R′=-pClC₆ H₄, BuSnCl[A₂ L₂], Complex 4

Scheme 2

where

-CHR=-CH₂ CH₂, R′=-C₆ H₅, BuSn[(A₁)₂ L₁], Complex 5

R=-CH(CH₃)CH₂ CH₃, R′=-C₆ H₅, BuSn[(A₂)₂ L₁], Complex 6

R=-CH(CH₃)CH₂ CH₃, R′=-pClC₆ H₄, BuSn[(A₂)₂ L₂], Complex 7

R=-CH(CH₃)CH₂ CH₃, R′=-CH₃, BuSn[(A₂)₂ L₃], Complex 8

In these reactions, NaCl was formed, which was filtered off. The excess solvent was removed under reduced pressure. The colored solids thus obtained were recrystallized from chloroform-petroleum ether in 63–73% yield. The complexes of the types BuSnClAL and BuSn[(A)₂ L] are dimers and monomers, respectively, as revealed by molecular weight measurements of these complexes. Plausible structures of these organic-inorganic hybrid formulations of monobutyltin(IV) have been suggested with the aid of spectral [IR and NMR (¹H, ¹³C and ¹¹⁹Sn)] evidences.

Spectral studies

IR spectra

The IR spectra of new N-protected amino acids and sterically congested heterocyclic β-diketone-modified BuSnCl₃ formulations and the corresponding ligands were recorded as KBr pellets in the region 4000–400 cm^-1 and 700–30 cm^-1. IR spectra of these organic-inorganic hybrid formulations of monobutyltin(IV) exhibit two medium intensity bands in the regions 610–620 cm^-1 and 530–540 cm^-1, which may be assigned to Sn-O bonds (Sharma et al., 2007). The IR spectra of N-protected amino acids show bands as 1770 cm^-1 and at 1390 cm^-1 which may be due to the imido ν(CO)_asym and ν(COO)_sym vibrations, respectively. A broad band was observed at 1690–1740 cm^-1, which may be due to the merging of ν(CO)_sym and ν(COO)_asym bands. In the complexes, this broad band split into two bands. ν(CO)_sym vibration appeared as a sharp band at 1720 cm^-1, and ν(COO)_asym vibration was present as a medium intensity band at 1610–1670 cm^-1. The band observed at 1390–1400 cm^-1 may be due to ν(COO)_sym vibrations. The value of Δν [Δν=ν(COO)_asym-ν(COO)_sym] for these N-protected amino acids and sterically congested heterocyclic β-diketone-modified BuSnCl₃ formulations was of the order of 210–270 cm^-1. This value of Δν indicates that N-protected amino acids are behaving as chelating bidentate ligands (Sharma et al., 2007). In the IR spectra of sterically congested heterocyclic β-diketones, ν(>C=O) stretching vibrations appeared at 1545 cm^-1. This band was observed at 1530 cm^-1 in the IR spectra of the complexes. This shift in the position of ν(>C=O) stretching vibrations toward lower wave number indicates the bidentate nature of sterically congested heterocyclic β-diketones in these complexes (Gupta et al., 2010). The bands present at 1590 cm^-1 and at 1560–1570 cm^-1 may be assigned to phenyl and ν(>C=C</>C=N-) stretching, respectively. The strong bands observed in the region 410–440 cm^-1 and 490 cm^-1 may be assigned to Sn-C vibrations (Sharma et al., 2007). In the IR spectra of the complexes of the type BuSnClAL, the band present at 230 cm^-1 may be assigned to ν(Sn-Cl-Sn), which indicates that chlorine is bridging between two tin atoms (Dubey and Singh, 2013).

¹H NMR spectra

The ¹H NMR spectra of new N-protected amino acids and sterically congested heterocyclic β-diketone-modified BuSnCl₃ formulations were recorded in CDCl₃ solutions using TMS as an internal standard and are summarized in Table 1. The broad signals of the carboxylic-OH of the N-protected amino acids and enolic-OH of sterically congested heterocyclic β-diketones appeared in the region δ 8.80–10.62 and δ 11.37–12.77, respectively. These broad signals were absent in the ¹H NMR spectra of the complexes. This shows deprotonation of N-protected amino acids and sterically congested heterocyclic β-diketones and also supports the formation of Sn-O bonds. The aromatic protons of N-protected amino acids appeared as a complex pattern in the region of δ 7.07–7.99 in these complexes, while aromatic protons of sterically congested heterocyclic β-diketones are overlapping with the aromatic protons of N-protected amino acids. The butyl protons attached to the central tin atom are present in the region δ 0.81–2.61.

Table 1

¹H NMR data of N-protected amino acids and sterically congested heterocyclic β-diketones and their monobutyltin(IV) complexes (in δ ppm).

Complex no.	Ligands and complexes											Sn-butyl
		COOH	C₆ H₄	CH	CH₂	CH₃	OH	Ring CH₃	Ring C₆ H₅	Terminal
		COOH	C₆ H₄	CH	CH₂	CH₃	OH	Ring CH₃	Ring C₆ H₅	C₆ H₅/-pClC₆ H₄	CH₃
	A₁ H^a	8.80(bs)	7.76(m)		2.81(t)
					4.00(t)
	L₁ H^b						12.77(bs)	2.08(s)	7.25–7.93(m)	*
1	BuSnCl[A₁ L₁]	–	7.16–7.99(m)	–	2.73(t)		–	**	***	***		0.86–2.50(m)
					3.97(t)
	L₂ H^b						11.37(bs)	2.14(s)	7.26–8.00(m)	*
	L₃ H^b						11.51(bs)	2.51(s)	7.17–7.83(m)		2.45(s)
2	BuSnCl[A₁ L₃]	–	7.09–7.96(m)	–	2.76(t)		–	**	***		**	0.92–2.48(m)
					4.02(t)
	A₂ H^c	10.62(bs)	7.28–7.88(m)	4.76(d)	1.54(m)	0.86(t)
				2.55(m)		1.12(d)
3	BuSnCl[A₂ L₁]	–	7.26–7.84(m)	4.70(d)**	**	**	–	**	***	***		0.86–2.53(m)
4	BuSnCl[A₂ L₂]	–	7.07–7.95(m)	4.66(d)**	**	**	–	**	***	***		0.82–2.61(m)
5	BuSn[(A₁)₂ L₁]	–	7.14–7.85(m)		2.73(t)		–	**	***	***		0.83–2.17(m)
					4.02(t)
6	BuSn[(A₂)₂ L₁]	–	7.14–7.85(m)	4.62(d)**	**	**	–	**	***	***		0.81–2.45(m)
7	BuSn[(A₂)₂ L₂]	–	7.15–7.83(m)	4.66(d)**	**	**	–	**	***	***		0.82–2.51(m)
8	BuSn[(A₂)₂ L₃]	–	7.25–7.86(m)	4.63(d)**	**	**	–	**	***		**	0.82–2.51(m)

Notes: (s), singlet; (t), triplet; (m), multiplet; (bs), broad singlet.

*Merged with phenyl region of hetrerocyclic β-diketones, **merged with butyl region, ***merged with phenyl region of N-protected amino acids.

^aRef. Sharma et al., 2007; ^bref. Gupta et al., 2010; ^cref. Gupta et al., 2009.

¹³C NMR spectra

The ¹³C NMR spectra of some new N-protected amino acids and sterically congested heterocyclic β-diketone-modified BuSnCl₃ formulations were recorded in CDCl₃ solution and given in Table 2. The mode of bonding of N-protected amino acids and sterically congested heterocyclic β-diketones in these organic-inorganic hybrid formulations of monobutyltin(IV) may be suggested by a comparative study of the ¹³C NMR spectra of these complexes and their parent ligands. The carboxylic carbon signal shows an upfield shift of the order of δ 1.0–3.5 in the ¹³C NMR spectra of these organic-inorganic hybrid formulations of monobutyltin(IV) in comparison with its position in the parent ligands. This indicates chelating bidentate nature of N-protected amino acids in these complexes. Imido CO is not involved in bonding as there was no significant shift in the position of imido carbon signal in the complexes compared to its position in the parent ligands. The other ligand involved in the formation of these organic-inorganic hybrid formulations of monobutyltin(IV) is sterically congested heterocyclic β-diketones. In the ¹³C NMR spectra of the complexes, there is small shift in the positions of C₃, C₄, and C₆ carbon signals due to delocalization of electrons in the complexes. This reveals the bidentate nature of sterically congested heterocyclic β-diketones in these organic-inorganic hybrid formulations of monobutyltin(IV). The carbon signals for butyl group appended to tin appeared in the region δ 13.5–35.2.

Table 2

¹³C NMR data of N-protected amino acids and sterically congested heterocyclic β-diketones and their monobutyltin(IV) complexes ( in δ ppm).

Complex no.	Ligands and complexes															Sn butyl
		COOH	CO	CH₃	CH₂	CH	C₆ H₄	Terminal		Ring C₆ H₅	C₃	C₄	C₅	C₆	C₇
		COOH	CO	CH₃	CH₂	CH	C₆ H₄	CH₃	-C₆ H₅/-p-ClC₆ H₄		C₃	C₄	C₅	C₆	C₇
	A₁ H^a	172.2	167.2		32.4		123.4
					34.1		133.1
							134.2

	L₁ H^b								131.9	147.9	161.4	103.5	137.5	192.0	15.8
									128.7	129.1
									128.4	127.8
									126.6	120.7
1	BuSnCl[A₁ L₁]	171.2	167.8		**	–	*		*	149.3–120.7	162.4	105.5	137.1	195.1	16.8	13.6
																25.8
																28.4
																35.1
	A₂ H^c	174.6	167.8	16.8	25.8	56.9 (CH-N)	134.2
				10.9		34.3	131.5
							123.6
3	BuSnCl[A₂ L₁]	171.2	168.0	**	**	51.9	*		*	149.4–120.2	162.3	105.4	137.1	194.8	16.8	13.6
						(CH-N)										25.7
																27.2
																33.7
	L₂ H^b								138.0	147.6	161.1	103.5	138.1	190.9	15.8
									136.2	129.1
									129.0	128.8
									126.8	120.8
4	BuSnCl[A₂ L₂]	171.2	167.8	**	**	55.8 (CH-N)	*		*	149.4–120.9	162.1	105.6	137.1	195.1	16.8	13.6
																25.7
																27.2
																35.2
6	BuSn[(A₂)₂ L₁]	171.1	167.8	**	**	51.7 (CH-N)	*		*	149.2–120.1	162.0	105.6	137.0	193.5	16.7	13.5
																25.5
																27.1
																33.6
7	BuSn[(A₂)₂ L₂]	171.2	167.9	**	**	51.9 (CH-N)	*		*	149.3–120.2	162.1	105.5	137.1	193.5	16.8	13.6
																25.7
																27.2
																33.7
	L₃ H^b							26.2		147.0	160.4	104.1	137.1	196.2	15.4
										129.2
										126.1
										120.4
8	BuSn[(A₂)₂ L₃]	171.2	167.9	**	**	51.9 (CH-N)	*	26.8	*	149.4–120.2	162.3	105.6	137.2	194.8	16.8	13.6
																25.7
																27.8
																33.7

¹J (¹¹⁹Sn-¹³C) values for the complex 1=961 Hz, Complex 4=991 Hz, and Complex 8=1021 Hz.

*Merged with phenyl region of hetrerocyclic β-diketones, **merged with butyl region.

^aRef. Sharma et al., 2007; ^bref. Gupta et al., 2010; ^cref. Gupta et al., 2009.

¹¹⁹Sn NMR spectra

The ¹¹⁹Sn NMR spectra of some representative N-protected amino acids and sterically congested heterocyclic β-diketone-modified BuSnCl₃ formulations were recorded in CDCl₃ solution. ¹¹⁹Sn NMR spectra of organic-inorganic hybrid formulations of monobutyltin(IV) of the types BuSnCl[A₂ L₁], BuSnCl[A₂ L₂], and BuSn[(A₂)₂ L₁] exhibit signals in the region δ-509.04 to 514.37. These organic-inorganic hybrid formulations of monobutyltin(IV) contain seven coordinated tin centers as indicated by ¹¹⁹Sn NMR chemical shift values, which are in agreement with the reported values for seven coordinated organotin(IV) complexes (Yin et al., 2007). ¹¹⁹Sn NMR spectra of the complexes of the types BuSnCl[A₂ L₁] and BuSnCl[A₂ L₂] show splitting of signals, which indicates the possibility of geometrical isomers.

Structure I

where

-CHR=-CH₂ CH₂,	R′=-C₆ H₅,	BuSnCl[A₁ L₁],	Complex 1
-CHR=-CH₂ CH₂,	R′=-CH₃,	BuSnCl[A₁ L₃],	Complex 2
R=-CH(CH₃)CH₂ CH₃	=-C₆ H₅,	BuSnCl[A₂ L₁],	Complex 3
R=-CH(CH₃)CH₂ CH₃	R′=-pClC₆ H₄,	BuSnCl[A₂ L₂],	Complex 4

Structure II

where

-CHR=-CH₂ CH₂,	R′=-C₆ H₅,	BuSn[(A₁)₂ L₁],	Complex 5
R=-CH(CH₃)CH₂ CH₃,	R′=-C₆ H₅,	BuSn[(A₂)₂ L₁],	Complex 6
R=-CH(CH₃)CH₂ CH₃,	R′=-pClC₆ H₄,	BuSn[(A₂)₂ L₂],	Complex 7
R=-CH(CH₃)CH₂ CH₃,	R′=-CH₃,	BuSn[(A₂)₂ L₃],	Complex 8

Conclusion

Some new N-protected amino acids and sterically congested heterocyclic β-diketone-modified BuSnCl₃ formulations of the types BuSnCl[AL] and BuSn[(A)₂ L] were prepared, and their plausible structures were suggested on the basis of physicochemical and multinuclear NMR spectra studied. N-protected amino acids and sterically congested heterocyclic β-diketones are behaving as bidentate ligands in these complexes as revealed by spectral evidence. The complexes of the types BuSnCl[AL] and BuSn[(A)₂ L] were found to be dimeric and monomeric in nature, respectively, as revealed by molecular weight measurements. Plausible structures (Structure I and Structure II) for these organic-inorganic hybrid formulations of monobutyltin(IV) of the types BuSnCl[AL] and BuSn[(A)₂ L], respectively, were proposed with the help of physicochemical and spectral studies.

N-protected amino acids and sterically congested heterocyclic β-diketones-modified BuSnCl₃ formulations of the types BuSnCl[AL] and BuSn[(A)₂ L] contain seven coordinated tin centers as revealed by ¹¹⁹Sn NMR chemical shift values (-509.04 to -514.37). A distorted pentagonal bipyramidal may be suggested for these organic-inorganic hybrid formulations of monobutyltin(IV).

Experimental

The ligands, N-protected amino acids and sterically congested heterocyclic β-diketones were prepared by reported methods. BuSnCl₃ is commercially available and was distilled before use. The experimental work and the chemical reactions were carried out under strictly anhydrous conditions. The solvents were dried by standard methods. Tin was estimated as tin(IV) oxide, while chlorine was estimated volumetrically by Volhard’s method. Molecular weights of these organic-inorganic hybrid formulations of monobutyltin(IV) trichloride (Acros Organics, NJ, USA) were determined by Rast method. Melting points of these complexes were determined in sealed capillaries. IR spectra of the samples were recorded as KBr pellets in the region 4000–400 cm^-1 on SHIMADZUFTIR-8400s spectrophotometer. ¹H and ¹³C NMR spectra of the complexes and the ligands were recorded in CDCl₃ solution on JEOLFTAL 300 NMR spectrometer operating at 300 and 75.45 MHz, respectively. ¹¹⁹Sn NMR spectra were recorded on Bruker Avance II 400 NMR spectrometer operating at 400 and 149.21 MHz, respectively.

Synthesis of N-protected amino acids and sterically congested heterocyclic β-diketone-modified BuSnCl₃ formulations

Organic-inorganic hybrid formulations of monobutyltin(IV) were synthesized by a similar method, and hence, the experimental details of a representative complex are given, and the data for other complexes are summarized in Table 3.

Table 3

Physical and analytical data of organic-inorganic hybrid formulations of monobutyltin(IV).

Complex no.	Complex formula	Reagents in gm (mmol)				NaCl in gm found (calc.)	% C found (calc.)	% H found (calc.)	% N found (calc.)	% Sn found (calc.)	% Cl found (calc.)	Physical state^a% Yield	Color M.P. °C	Mol. Weight found (calc.)
Complex no.	Complex formula	BuSnCl₃	Na	AH	LH	NaCl in gm found (calc.)	% C found (calc.)	% H found (calc.)	% N found (calc.)	% Sn found (calc.)	% Cl found (calc.)	Physical state^a% Yield	Color M.P. °C	Mol. Weight found (calc.)
1	BuSnCl[A₁ L₁]	0.99	0.16	0.77	0.98	0.40				16.78	5.00	68	Yellow	1393
		(3.53)	(7.06)	(3.53)	(3.53)	(0.41)				(16.79)	(5.01)		92	(706.76)
2	BuSnCl[A₁ L₃]	1.17	0.19	0.91	0.89	0.48	50.77	4.60	6.35	18.40	5.48	63	Light brown	1278
		(4.15)	(8.31)	(4.15)	(4.15)	(0.48)	(50.30)	(4.37)	(6.51)	(18.41)	(5.49)		90	(644.69)
3	BuSnCl[A₂ L₁]	1.01	0.16	0.93	0.99	0.41	56.10	4.80	5.59	15.84	4.72	65	Yellow	1485
		(3.59)	(7.19)	(3.59)	(3.59)	(0.42)	(56.13)	(4.84)	(5.61)	(15.85)	(4.73)		86	(748.84)
4	BuSnCl[A₂ L₂]	1.11	0.18	1.03	1.23	0.45	53.52	4.48	5.31	15.13	4.52	69	Yellow	1554
		(3.96)	(7.93)	(3.96)	(3.96)	(0.46)	(53.66)	(4.50)	(5.36)	(15.15)	(4.53)		88	(783.28)
5	BuSn[(A₁)₂ L₁]	0.89	0.21	1.38	0.87	0.55	57.99	4.28	6.22	13.32		71	Yellow	879
		(3.15)	(9.47)	(6.31)	(3.15)	(0.55)	(58.06)	(4.30)	(6.29)	(13.34)			77	(889.49)
6	BuSn[(A₂)₂ L₁]	0.62	0.15	1.15	0.61	0.37	60.40	5.12	5.71	12.17		70	Reddish yellow	965
		(2.20)	(6.60)	(4.40)	(2.20)	(0.38)	(60.44)	(5.17)	(5.75)	(12.19)			78	(973.65)
7	BuSn[(A₂)₂ L₂]	0.66	0.16	1.22	0.73	0.41	58.32	4.86	5.51	11.75		73	yellow	1001
		(2.35)	(7.05)	(4.69)	(2.35)	(0.41)	(58.37)	(4.89)	(5.55)	(11.77)			82	(1008.10)
8	BuSn[(A₂)₂ L₃]	0.71	0.17	1.32	0.54	0.42				13.01		72	Light brown	901
		(2.53)	(7.61)	(5.07)	(2.53)	(0.43)				(13.02)			76	(911.58)

^aSolid.

A₁ H=N-phthaloyl β-alanine, A₂ H=N-phthaloyl iso-leucine.

, .

N-phthaloyl β-alanine (0.77 g, 3.53 mmol) and 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one (0.98 g, 3.53 mmol) were dissolved in THF. A THF solution of the ligands was added to a methanolic solution of sodium (0.16 g, 7.06 mmol), and the reaction mixture was refluxed for ∼5 h. Then, a THF solution of BuSnCl₃ (0.99 g, 3.53 mmol) was added dropwise with constant stirring to the solution of sodium salts of the two ligands, and the reaction mixture was further refluxed for ∼8 h. After this, the reaction mixture was filtered to remove NaCl formed in the reaction. A yellow solid was isolated after removing the excess solvent under the reduced pressure. The product was recrystallized from chloroform-petroleum ether mixture. The physical and analytical details of this organic-inorganic hybrid formulation of monobutyltin(IV) and other analogous formulations are given in Table 3.

Corresponding author: Sanjiv Saxena, Department of Chemistry, University of Rajasthan, Jaipur 302004, India, e-mail: saxenas348@rediffmail.com

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Received: 2014-1-30

Accepted: 2014-6-9

Published Online: 2014-7-19

Published in Print: 2014-7-1

This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Articles in the same Issue

https://doi.org/10.1515/mgmc-2014-0001

Keywords for this article

BuSnCl3; heterocyclic β-diketones; N-protected amino acids; spectral studies

Creative Commons

BY-NC-ND 3.0

Coordination propensity of N-protected amino acids and sterically congested heterocyclic β-diketones toward BuSnCl3: preparation and structural features of some new seven coordinated organic-inorganic hybrid formulations of monobutyltin(IV)

Article

Abstract

Introduction

Results and discussion

Spectral studies

IR spectra

1H NMR spectra

13C NMR spectra

119Sn NMR spectra

Conclusion

Experimental

Synthesis of N-protected amino acids and sterically congested heterocyclic β-diketone-modified BuSnCl3 formulations

References

Articles in the same Issue

Articles in the same Issue

Articles in the same Issue

Coordination propensity of N-protected amino acids and sterically congested heterocyclic β-diketones toward BuSnCl₃: preparation and structural features of some new seven coordinated organic-inorganic hybrid formulations of monobutyltin(IV)

¹H NMR spectra

¹³C NMR spectra

¹¹⁹Sn NMR spectra

Synthesis of N-protected amino acids and sterically congested heterocyclic β-diketone-modified BuSnCl₃ formulations