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Nitrite ion with an O-N-O bond angle of ca. 120°

Space-filling model of the nitrite ion

The nitrite ion has the chemical formula NO₂⁻. The anion is symmetric with equal N-O bond lengths and a O-N-O bond angle of about 120°. On protonation the unstable weak acid nitrous acid is produced. Nitrite can be oxidized or reduced, with product somewhat dependent on the oxidizing/reducing agent. The nitrite ion is an ambidentate ligand and is known to bond to metal centers in at least five different ways.^[1] Nitrite is important in biochemistry as a source of the vasodilator nitric oxide. Nitrites are used for curing meat. In organic chemistry the NO₂ group is present in nitrous acid esters and nitro compounds.

The nitrite ion[link]

Nitrite salts[link]

Sodium nitrite is made industrially by passing nitrous fumes into aqueous sodium hydroxide or sodium carbonate solution.^[1]

NO + NO₂ + 2NaOH (or Na₂CO₃) → 2NaNO₂ +H₂O ( or CO₂)

The product is purified by recrystallization. Alkali metal nitrites are thermally stable up to and beyond the melting point (441 °C for KNO₂). Ammonium nitrite can be made from dinitrogen trioxide, N₂O₃, which is formally the anhydride of nitrous acid.

2NH₃ + H₂O +N₂O₃ → 2NH₄NO₂

This compound may decompose explosively on heating.

In organic chemistry nitrites are used in diazotization reactions.

Structure[link]

The two canonical structures of NO₂⁻, which contribute to the resonance hybrid for the nitrite ion

The nitrite ion has a symmetrical structure (C_2v symmetry) with both N-O bonds having equal length. In valence bond theory it is described as a resonance hybrid with equal contributions from two canonical forms that are mirror images of each other. In molecular orbital theory there is a sigma bond between each oxygen atom and the nitrogen atom, and a delocalized pi bond made from the p orbitals on nitrogen and oxygen atoms which are perpendicular to the plane of the molecule. The negative charge of the ion is equally distributed on the two oxygen atoms. Both nitrogen and oxygen atoms carry a lone pair of electrons. Therefore the nitrite ion is a Lewis base. Moreover, it can act as an ambidentate ligand towards a metal ion, donating a pair of electrons from either nitrogen or oxygen atoms.

Acid-base properties[link]

Dimensions of trans HONO (from the microwave spectrum)

In aqueous solution nitrous acid is a weak acid.

HNO₂ H⁺ + NO₂^-; pK_a = ca. 3.3 at 18 °C^[2]

Nitrous acid is volatile; in the gas phase it exists predominantly as a trans- planar molecule. In solution it is unstable with respect to the disproportionation reaction

3HNO₂ (aq) H₃O⁺ + NO₃^- + 2NO

This reaction is slow at 0 °C.^[1] Addition of acid to a solution of a nitrite in the presence of a reducing agent such as iron(II) is a way to make nitric oxide, NO, in the laboratory.

Oxidation and reduction[link]

The formal oxidation state of the nitrogen atom in a nitrite is +3. This means that it is can be either oxidised to oxidation states +4 and +5 or reduced to oxidation states as low as -3. Standard reduction potentials for reactions directly involving nitrous acid are shown in the table.^[3]

Half-reaction	E0/V
NO3- + 3H+ + 2e- HNO2 + H2O	+0.94
2HNO2+ 4H+ + 4e- H2N2O2 + 2H2O	+0.86
N2O4 + 2H+ + 2e- 2HNO2	+1.065
2HNO2+ 4H+ + 4e- N2O + 3H2O	+1.29

The data can be extended to include products in lower oxidation states. For example,

H₂N₂O₂ + 2H⁺ + 2e^- N₂ + 2H₂O; E⁰ = 2.65V

Oxidation reactions usually result in the formation of the nitrate ion, with nitrogen in oxidation state +5. For example, oxidation with permanganate can be used for quantitative analysis of nitrite, by titration.

5NO₂^- + 2MnO₄^- + 6H⁺ → 5NO₃^- + 2Mn²⁺ + 3H₂O

The product of reduction reactions are various depending on the reducing agent used. With sulfur dioxide the products are NO and N₂O; with tin(II), Sn²⁺, the product is hyponitrous acid, H₂N₂O₂; reduction all the way to ammonia occurs with hydrogen sulfide. With the hydrazinium cation, N₂H₅⁺, hydrogen azide, HN₃, is produced

HNO₂ + N₂H₅⁺ → HN₃ + H₂O + H₃O⁺

which can also further react with nitrite

HNO₂ + HN₃ → N₂O + N₂ + H₂O

This reaction is unusual in that it involves compounds with nitrogen in four different oxidation states.^[1]

Coordination complexes[link]

The nitrite ion is known to form complexes in at least five different ways.^[1]

1. When donation is from nitrogen to a metal centre, the complex is known as a nitro- complex.
2. When donation is from one oxygen to a metal centre, the complex is known as a nitrito- complex.
3. Both oxygen atom may donate to a metal centre, forming a chelate complex.
4. A nitrite ion can form an unsymmetrical bridge between two metal centres, donating through nitrogen to one metal and oxygen to the other.
5. A single oxygen atom can bridge to two metal centres.

Alfred Werner studied the nitro-nitrito isomerism (1 and 2) extensively. The red isomer of cobalt pentammine with nitrite is now known to be a nitrito complex, [Co(NH₃)₅(ONO)]²⁺; it is metastable and isomerizes to the yellow, nitro complex [Co(NH₃)₅(NO₂)]²⁺. An example of chelating nitrite (3) was found in [Cu(bipy)₂(O₂N)]NO₃; bipy is the bidentate ligand 2,2'bypyridyl and the two bipy ligands occupy four coordination sites on the copper ion so the nitrite is forced to occupy two sites in order to achieve an octahedral environment around the copper ion. Examples of 4 and 5 are illustrated.^[1]

Nitrite in biochemistry[link]

Sodium nitrite is used for the curing of meat because it prevents bacterial growth and, in a reaction with the meat's myoglobin, gives the product a desirable dark red color. Because of the toxicity of nitrite (the lethal dose of nitrite for humans is about 22 mg per kg body weight), the maximum allowed nitrite concentration in meat products is 200 ppm. Under certain conditions, especially during cooking, nitrites in meat can react with degradation products of amino acids, forming nitrosamines, which are known carcinogens.^[4]

Nitrite is detected and analyzed by the Griess Reaction, involving the formation of a deep red-colored azo dye upon treatment of a NO₂⁻-containing sample with sulfanilic acid and naphthyl-1-amine in the presence of acid.^[5] Nitrite can be reduced to nitric oxide or ammonia by many species of bacteria. Under hypoxic conditions, nitrite may release nitric oxide, which causes potent vasodilation. Several mechanisms for nitrite conversion to NO have been described including enzymatic reduction by xanthine oxidoreductase, nitrite reductase and NO synthase (NOS), as well as nonenzymatic acidic disproportionation.

Organic nitrites and nitro compounds[link]

A nitrite ester

aromatic nitration

In organic chemistry, nitrites are esters of nitrous acid and contain the nitrosooxy functional group. Nitro compounds contain the C-NO₂ group. Nitrites have the general formula RONO, where R is an aryl or alkyl group. Amyl nitrite is used in medicine for the treatment of heart diseases. A classic named reaction for the synthesis of alkyl nitrites is the Meyer synthesis^[6][7] in which alkyl halides react with metallic nitrites to a mixture to nitroalkanes and nitrites.

Nitrobenzene is a simple example of a nitro compound. In aromatic nitration reaction a C-H bond is broken, leaving the two electrons on the carbon atom. The two electrons are added to the nitronium ion reducing it to nitrite.

See also[link]

• Curing (food preservation)

References[link]

External links[link]

• Material Safety Data Sheet, sodium nitrite
• ATSDR - Case Studies in Environmental Medicine - Nitrate/Nitrite Toxicity U.S. Department of Health and Human Services (public domain)

Bibliography[link]

• Greenwood, N. N.; Earnshaw, A. (1997). Chemistry of the Elements (2nd ed.). Butterworth–Heinemann. ISBN 0080379419. 

Romeo Miller
Miller in 2009
Background information
Birth name	Percy Romeo Miller, Jr.[1]
Also known as	Lil' Romeo, Rome, Romeo
Born	(1989-08-19) August 19, 1989 (age 22)[1] New Orleans, Louisiana, United States[1]
Genres	Hip hop
Occupations	Rapper Model Basketball player Entrepreneur Actor
Years active	2001–present
Labels	No Limit (2001–2002) Priority (2001–2002) The New No Limit (2002–2004) Universal (2002–2003) E1 (2004–2005) Guttar Music (2005–2006) Take A Stand (2007–present) The Next Generation (CEO) (2010–present) No Limit Forever (CEO) (2010–present)
Website	romeoforever.com

Percy Romeo Miller, Jr. (born August 19, 1989),^[2] better known by his stage name Romeo (previously Lil' Romeo), is an American rapper, actor, basketball player, entrepreneur, and model. As a rap musician, Miller has released three studio albums and two compilation albums.

Early life[link]

Romeo Miller was born in New Orleans, Louisiana. He is the son of rapper and entrepreneur Master P and former rapper Sonya C. He is the nephew of rappers C-Murder and Silkk the Shocker and the brother of singer Cymphonique. Romeo was signed to No Limit at the age of 5 after he wrote a rap to his dad.

Music career[link]

[edit] Lil' Romeo (2001)

He then released his debut album 7 years later titled after his original alias Lil' Romeo. This offering contained the hit single "My Baby" that charted No. 1 on the Hot R&B/Hip-hop Singles. The album peaked at No. 6 on the Billboard 200 and No. 5 on the Top R&B/Hip-Hop Albums,selling more than 500,000 copies the first week out making it certified Gold. The album is now certified certified Platinum by the RIAA for the sales of 1,300,000. Also in 2001 he was featured on his uncle Silkk the Shocker's remix single of "That's Kool", which was also featured on his own album.

[edit] Game Time (2002–2003)

In 2002, a year later after his debut album, Miller put out his second studio album, Game Time. It peaked at No. 33 on the Billboard 200 and No. 10 on the Top R&B/Hip-Hop Albums selling close to a 110,000 copies the first week .^[1] It spawned the billboard charting single "2-Way" that charted to No. 66 Hot R&B/Hip-Hop Songs. It also spawned the album second single "True Love" which charted at No. 16 under the Hot 100 Singles. Though not as successful on the charts as Miller's debut album It still was successful in sales certified 2x Platinum, selling 2,430,785 copies making this Miller's highest selling album.

[edit] Romeoland (2004–2007)

In 2004, miller released his third studio album Romeoland, which was not as successful as his last two albums selling 50,000 the first week, but still managed to be certified Gold selling over 459,000 copies in the United States.^[1] It was also the last studio album to feature Miller billed as Lil' Romeo. In 2005 Romeo along with his brother Valentino Miller who was known as Young V at that time and their three cousins C-Los, Lil' D & Willie J formed the group Rich Boyz & released their debut album Young Ballers: The Hood Been Good to Us. In 2006 Miller released a compilation album entitled Greatest Hits the album featured all of his hit songs when Miller was billed as Lil' Romeo. In 2006 Romeo released the two albums Lottery & God's Gift on the new label owned by himself and his father Master P, entitled Guttar Music. Lottery served as Millers first independent release while God's Gift served as a soundtrack to a movie with the same name. God's Gift was also Miller's first album to use the name Romeo and to have explicit language.^[1] The two albums were also known for containing Miller's single "U Can't Shine Like Me" which was a direct response to Bow Wow, who fans thought dissed Miller in his song "Fresh Azimiz". In 2007 Miller released a collaboration album with his father Master P titled Hip Hop History it sold 32,000 records worldwide.

[edit] Intelligent Hoodlum (2008–present)

In 2008 Miller stated he was working on his fourth studio album entitled Gumbo Station.^[3] On June 17, 2008 Miller released the first single from the album which was "Get Low wit It" which featured Akon & his brother Valentino Miller it failed to gain success on the Billboard charts.^[4]

On March 3, 2009 Romeo released a compilation entitled Get Low LP that contained songs that were supposed to be on Gumbo Station. It debuted at No. 149 on the Billboard 200 and as of May 5, 2009 it has sold over 20,000 copies. In 2010 Romeo confirmed that he was still working on his fourth studio album but he changed the name of the album to The College Boy. Romeo then announced that the title of the album was going to be I Am No Limit.

On January 19, 2010 Romeo released the first promotional single for the album entitled "Tell Me A Million Times" that featured Tempo.^[5] Then on January 26, 2010 Romeo released the second promotional single for the album entitled "Ice Cream Man Jr." which was a tribute to his dad Master P.^[6] On February 16, 2010 Miller released his debut mixtape Patience Is A Virtue to promote the album.^[7] Then on March 2, 2010 Romeo released two EPs to promote the album which were the Famous Girl & Monster/Practice.^[8][9] Also In 2010 Miller debuted his newly founded record label The Next Generation Entertainment with his new group the College Boyys.^[10] They released a collaboration album on May 25, 2010 entitled Spring Break which sold over 200,000 copies worldwide.^{[11][dead link]} Miller also on this day released three singles which were "You" that featured D'Anna & Lil Twist, "She Bad" that featured Millers cousins Lil' D & Black Don & "They Dont Know" but all of the singles failed to reach the charts.^[12][13][14] Romeo also performed at the 2010 Hip Hop Honors along with his brother Valentino Miller, his cousins Lil' D & Black Don, & his uncle Silkk The Shocker, along with Trina, Gucci Mane & Mystikal to honor his dad Master P & No Limit Records.^[15] In late 2010 Romeo relaunched No Limit as No Limit Forever Romeo also confirmed that he has changed the name of the album from I Am No Limit to Intelligent Hoodlum.^[16]

In 2011 It was confirmed that Romeo is going on a new tour with his dad Master P & his uncle Silkk the Shocker the tour is entitled ”No Limit Forever International".^[17] On January 11, 2011 Romeo released his EP Dont Push Me.^[18] On May 3, 2011 Romeo released the first official single from Intelligent Hoodlum which is "Famous Girl (Remix)" which is really the mastered version of the original it still features appearances from Sean Kingston & Miller's cousin Black Don.^[19] On August 19, 2011 Romeo released his I Am No Limit mixtape which was originally supposed to be his fourth studio album before it got changed but Miller just decided it would be best to just release it as a mixtape for his fans.^[20][21][22]

In 2012 Romeo formed a new group called RESQ3 they released their first single "The Only One" & supposed to be releasing a album in some time.^[23] Even though Romeo has created his new group he is still working & planning on releasing his fourth studio album Intelligent Hoodlum. On April 12, 2012 he released his first single from the album entitled "Hug Me Forever" which features his brother Valentino & his artist Kyros & has already shot the official music video for it.^[24] On May 19, 2012 Romeo released the music video for "Hug Me Forever" it was directed by Corey Molina of Creative Dream Productions.^[25]

Other ventures[link]

Acting career[link]

Miller started his acting career with a cameo appearance in the 2001 film Max Keeble's Big Move, as himself.^[26] He later co-starred with Jessica Alba, Mekhi Phifer and Zachary Isaiah Williams in the film Honey (2003). In Honey, his character was Benny, a young boy looking for a break.^[27] Also in 2003, he voiced himself on an episode of the animated series, Static Shock, to which he had performed the theme song.^[28] He co-starred with his dad in a movie called Uncle P in 2005.^{[citation needed]} He also starred in another movie with Zachary Isaiah Williams, God's Gift, which came out in 2006. Recently, he made a cameo appearance, as himself, in Ned's Declassified School Survival Guide as a rapping coach for the teachers. Then in 2007 he starred in film ASL as himself, Rome, alongside Forrest Lipton and Zachary Isaiah Williams who played the young Romeo; Lil Romey and had also previously starred with Romeo in Honey and Nickelodeon's Romeo!. He guest-starred as a rapper accused of murder in the 2010 CBS series, The Defenders and acted in the highly successful film, Jumping the Broom, released in May 2011. In 2011, he also starred in TV commercials for McDonald's & ICDC Colleges.

Fashion designer[link]

On July 24, 2010 Romeo launched his own clothing line titled "College Boyys", which has also been promoted by Miller & his new group the College Boyys. It has also been promoted by artists such as Justin Bieber, Big Time Rush & Jaden Smith.^[29] Romeo stated

Basketball career[link]

Percy Miller, Jr.
College	USC
Conference	Pac-10
Sport	Basketball
Position	Point guard
Jersey #	15
Nickname	Romeo, Prince P
Height	5 ft 11 in (1.80 m)
Weight	170 lb (77 kg)
Nationality	American
Born	(1989-08-19) August 19, 1989 (age 22) New Orleans, Louisiana
High school	Beverly Hills High School
Tournaments
2009 NCAA Tournament

Romeo was invited, in the summer of 2006, to the Reebok-sponsored ABCD Camp, which is considered the premier basketball camp in the United States. The Teaneck, New Jersey-based ABCD Camp is an invitation-only basketball showcase previously attended by high-profile players including Kobe Bryant, Stephon Marbury, Tracy McGrady, LeBron James and Carmelo Anthony. Surrounded by future NBA players such as O. J. Mayo, Derrick Rose, and Kevin Love, Miller looked out of place and averaged less than 2 points a game throughout the camp. The Wall Street Journal made an article on March 8, entitled "A Hot Prospect," cites Sonny Vaccaro, the longtime director of the ABCD Camp, as explaining, "he invited Romeo Miller to the 2006 camp, primarily as a favor to Percy Miller, whom he knew from the club basketball circuit." In the article, Vaccaro indicated, "If you're looking for the profile of an athlete who plays basketball at USC, he's not it."^[30]

On April 13, 2007, Miller verbally committed to the University of Southern California (USC) and signed a letter of intent on November 19, 2007.

Miller, a 5'11" point guard, was a four year starter at Beverly Hills High School. As a junior during the 2005–2006 high school season he averaged 13.9 points and 5.6 assists per game.^[31][32] As a senior during the 2006–2007 high school season he averaged 8.6 points and 9.0 assists per game.^[30][31]

According to The Wall Street Journal, it appears the decision to grant Miller a full scholarship at USC was largely driven by his relationship with friend and teammate Demar DeRozan, the 6-foot-6 All-American forward who was rated as the number five prospect in the country on Scout.com. The Wall Street Journal reported Coach Tim Floyd as saying, "Last April...Percy Miller called while driving both players from a tournament in Fayetteville, Ark...Percy Miller said 'Demar and Romeo are ready to make their decision, and would you like to have them both on scholarship?'...'I said absolutely.'"^[30] Miller and DeRozan began playing in the 2008–2009 season.

Modeling career[link]

On December 27 Romeo modeled for a new 2011 calendar.^[33] On April 10, 2011 Miller modeled for the April issue of TROIX magazine.^[34] On April 12, 2011 Miller modeled again for some new pictures.^[35] He also modeled with the singer-songwriter Chynna Terrell.

Dancing with the Stars[link]

After originally withdrawing from season two of Dancing with the Stars due to an injury,^[36] Romeo competed in season twelve.^[37] He was partnered with professional dancer, Chelsie Hightower. They were eliminated from the show on May 10, 2011 and finished in the Top 5, one week before the semi-final.

• In week 7, Donnie Burns was the guest judge and scored the dances.

Personal life[link]

Miller attended Beverly Hills High School in Beverly Hills, California. Romeo sponsors "Loco Tonic", an energy drink he mentions in his newer songs. In 2008, Romeo was ranked No. 18 in the most fit men in the world. Miller was born on Aug. 19, 1989 in New Orleans, La. He is the oldest of seven children from parents Percy, Sr. and Sonya Miller. His father is a business entrepreneur and musician. His father also shares a passion for the game of basketball and signed contracts with the Charlotte Hornets and Toronto Raptors. Percy wears the No. 15 because that is the number his father wore in high school. Miller also believes in giving back to the community and is involved in a variety for charity endeavors and in 2008 along with his father received the key to the city in Memphis in recognition of their "Let the Kids Grow" educational program.

Discography[link]

Filmography[link]

Felipe Solis is schedule to appear in Romeo's new reality show Romeo & Juliet

Awards and nominations[link]

• Billboard Music Awards
  • 2001, Rap Artist of the Year (Winner)
  • 2001, Music Videos: My Baby (Winner)
  • 2002, R&B/Hip-Hop: My Baby (Winner)
• Kids Choice Awards
  • 2004, Favorite Television Actor – Male for: Romeo! (Nominated)
  • 2005, Favorite Television Actor – Male for: Romeo! (Winner)
  • 2006, Favorite Television Actor – Male for: Romeo! (Nominated)
• Teen Choice Awards
  • 2004, Choice Breakout Movie Star – Male for: Honey (Nominated)
• Black Reel Awards
  • 2004, Choice Breakout Movie Star – Male for: Honey (Nominated)
• Young Artist Awards
  • 2005, Best Performance in a TV Series (Comedy or Drama) – Leading Young Actor: Romeo! (Nominated)
• NAMIC Vision Awards
  • 2005, Best Comedic Performance: Romeo! (Nominated)
• Image Awards
  • 2005, Outstanding Performance in a Youth/Children's Program – Series or Special: Romeo! (Nominated)

References[link]

External links[link]

Wikimedia Commons has media related to: Romeo Miller

• Official website
• USC Athletics Player Biography: No. 15 Percy Miller
• Romeo Miller's channel on YouTube
• Romeo on Myspace
• Romeo Miller on Twitter
• Romeo at the Internet Movie Database
• Photos from Shrink-A-Bulls